Tag: M.W=100-200

6065-82-3, In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 6065-82-3 as follows.

TMSOTf (55.2 muL, 305 mumol) was added to a suspension of 23 (31.8 mg, 50.8 mumol) and ethyl diethoxyacetate (27.3 muL, 152 mumol) in dichloroethane (2 mL), and the reaction mixture was heated at 100 C for 21.5 h. As a large amount of starting material still remained at this stage, TMSOTf (18.2 muL, 102 mumol) and ethyl diethoxyacetate (9.1 muL, 50.8 mumol) were added to the reaction mixture and the whole was heated at 100 C for 20.5 h. The reaction mixture was diluted with saturated NaHCO3 (10 mL) and extracted with chloroform (3¡Á30 mL). The combined extracts were washed with brine (30 mL), dried, and concentrated in vacuo to give a residue (60 mg). Chromatography of this residue on a silica gel (10 g) column with chloroform-methanol (100/1) gave 26a (16.1 mg, 46%) as a pale yellow oil. IR (KBr) 3375, 2927, 2854, 1734, 1645, 1460, 1178, 1058 cm-1; 1H NMR (CDCl3, 500 MHz) delta 1.289 (3H, t, J=7.2 Hz, OCH2CH3), 1.86 (3H, s, 12-CH3), 2.11 (3H, s, 3-CH3), 2.26 (1H, dd, J=17.1, 10.7 Hz, 14-Hbeta), 2.50 (3H, s, TsCH3), 2.55 (3H, s, NCH3), 2.78 (1H, d, J=17.4 Hz, 5-Hbeta), 2.97 (1H, dd, J=17.4, 7.6 Hz, 5-Halpha), 3.26 (1H, dd, J=17.1, 4.2 Hz, 14-Halpha), 3.69 (3H, s, 2-OCH3), 3.74 (3H, s, 11-OCH3), 3.83 (3H, s, 10-OCH3), 3.87 (3H, s, 1-OCH3), 3.86-3.90 (1H, overlapped, 6-H), 4.23 (2H, q, J=7.0 Hz, OCH2CH3), 4.24-4.29 (1H, m, 14a-H), 4.31 (1H, br s, 15-H), 4.70 (1H, br s, OH), 6.34 (1H, s, 9-H), 7.38 (2H, d, J=8.2 Hz, 2¡Á2′-H), 7.86 (2H, d, J=8.2 Hz, 2¡Á3′-H); 13C NMR (CDCl3, 125 Hz) delta 8.7 (3-CH3), 10.8 (12-CH3), 14.2 (OCH2CH3), 21.4 (TsCH3), 23.6 (C5), 26.5 (C14), 40.4 (NCH3), 51.2 (C9), 52.4 (C14a), 54.2 (C15), 58.6 (C6), 59.9 (10-OCH3), 60.0 (2-OCH3), 60.3 (1-OCH3), 60.6 (11-OCH3), 61.7 (OCH2CH3), 114.3 (C4a), 117.3 (C3), 122.4 (C9a), 123.0 (C15a), 125.0 (C13a), 127.1 (C12), 128.6 (2¡ÁCH), 129.7 (2¡ÁCH), 133.6 (C1′), 141.0 (C13), 144.7 (C1), 145.3 (C4′), 147.8 (C4), 148.9 (C10), 149.3 (C2), 149.6 (C11), 169.8 (C7), 171.4 (C16); FABMS m/z 711 [M+1]+; HRFABMS m/z 711.2585 (M++1, calcd for C36H43N2O11S, 711.2588).

According to the analysis of related databases, Ethyl diethoxyacetate, the application of this compound in the production field has become more and more popular.

Reference:
Article; Yokoya, Masashi; Shinada-Fujino, Kimiko; Yoshida, Saiko; Mimura, Masahiro; Takada, Hiroki; Saito, Naoki; Tetrahedron; vol. 68; 22; (2012); p. 4166 – 4181;,
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A common heterocyclic compound, 25597-16-4, name is Ethyl 4,4,4-trifluorocrotonate, molecular formula is C6H7F3O2, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route. 25597-16-4.

Step 2: ethyl 8-iodo-6-(trifluoromethoxy)-2-(trifluoromethyl)-2H-chromene-3-carboxylate The resulting product (2.5 g, 7.5 mmol) from step 1, triethylamine (2 mL) and ethyl 4,4,4-trifluorocrotonate (5.1 g, 30 mmol) were mixed in DMF (10 mL), and then the system was heated to 85 C. for reaction for 48 hrs. At the end of reaction, the reaction system was cooled to room temperature, added with water and extracted with ethyl acetate, and the organic phase was dried and evaporated in vacuum to obtain 2.5 g of the product (69%) by column chromatography. 1HNMR (400 MHz, d-CDCl3), delta 7.60 (s, 2H), 7.10 (s, 1H), 5.81 (m, 1H), 4.30 (dd, 2H), 1.33 (m, 3H) MS (MM-ES+APCI), m/z: 481 (M-H+)

The synthetic route of Ethyl 4,4,4-trifluorocrotonate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Guangzhou Institutes of Biomedicine and Health, Chinese Academy of Sciences; Zhang, Yanmei; Talley, John Jeffrey; Obukowicz, Mark G.; Tu, Zhengchao; Tortorella, Micky; Wang, Yican; Liu, Jianqi; Chen, Yan; Liu, Xiaorong; Lu, Xin; US2015/133538; (2015); A1;,
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140-11-4, Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 140-11-4, name is Benzyl acetate, A new synthetic method of this compound is introduced below.

Into a column (Omnifit (registered trademark), inner diameter: 10 mm), 1.55 g (about 2.4 mL) of an anion exchange resin (DOWEX (registered trademark) 1¡Á2 100-200 Mesh, Cl form) was packed, and the column was placed in a column oven whose temperature was adjusted to 60 C., stood vertically and fixed. Next, 60 mL of 1 mol/L sodium methoxide solution previously prepared was fed into the column at a rate of 1.0 mL/min (SV: 25 hr-1) using a syringe pump (manufactured by YMC CO., LTD.). Next, 60 mL of methanol was fed into the column at a rate of 1.0 mL/min (SV: 25 hr-1) using a syringe pump to wash the resin. Subsequently, 34 g of methanol was added to 6 g of benzyl acetate to prepare a homogeneous solution, the prepared solution was passed through the column at a rate of 1.0 mL/min (SV: 25 hr-1) using a syringe pump, and the reaction solution was collected from an outlet of the column. As a result, the reaction solution containing 4.28 g of desired benzyl alcohol was obtained (yield: 99%). It was possible to selectively remove methyl acetate produced as a by-product by concentration operation. In the obtained reaction solution, only methyl acetate was identified, and no acetic acid was identified. Although the reaction rate gradually decreased due to a long-time feeding, the resin was regenerated by feeding a sodium methoxide solution to the column after use, whereby the reaction rate was recovered to the initial reaction rate.

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Patent; KANEKA CORPORATION; MACHIDA, Koji; Yasukouchi, Hiroaki; Nishiyama, Akira; US2019/300465; (2019); A1;,
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34846-90-7, These common heterocyclic compound, 34846-90-7, name is Methyl 3-methoxyacrylate, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

A 1-L round-bottom flask was charged with /ert-butyl 4-oxopiperidine-l- carboxylate (Sigma Aldrich, 20.0 g, 100 mmol) and purged with nitrogen. THF (57 ml) was introduced, and the resultant solution cooled to -78 ¡ãC in a dry ice-acetone bath. A solution of potassium /ert-butoxide (1.6 M in THF, 80 mL, 128 mmol, 1.28 equiv) was added to the reaction mixture via syringe over 5 min. Following addition, the reaction mixture was allowed to warm to 0 ¡ãC in an ice-water bath. After 30 min, the peach colored reaction mixture was cooled to -78 ¡ãC. Methyl 3-methoxyacrylate (22.8 mL, 212 mmol, 2.11 equiv) was added dropwise to the reaction mixture via syringe over 5 min. Following addition, the reaction mixture was allowed to warm to ambient temperature. After 2 h, the resultant red reaction mixture was cooled was cooled to -78 ¡ãC. N-phenyl bis-trifluoromethane sulfonimide (56.7 g, 159 mmol, 1.58 equiv) was added to the vigorously stirred, cooled reaction mixture in one portion and the resultant reaction mixture was subsequently allowed to warm to 0 ¡ãC in an ice-water bath. After 1 h, saturated aqueous sodium bicarbonate solution (200 mL) and EtOAc (200 mL) were added to the reaction mixture, and the layers were separated. The aqueous layer was extracted with EtOAc (3150 mL), the combined organic layers were dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by flash column chromatography in two portions (340-g silica gel Biotage column, eluent: gradient, 0 to 30percent EtOAc in heptane with 1percent Et3N as an additive) to afford (E)-tert-butyl 3-(3-methoxy-3-oxoprop-1-en-1-yl)-4-(((trifluoromethyl)sulfonyl)oxy)-5,6-dihydropyridine-1(2H)-carboxylate (38.0 g, 91 mmol, 91percent yield) as a off-white solid.

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 34846-90-7.

Reference:
Patent; USA Anjin Corporation; M .weisi; B .C.miergelamu; T .dining; J .siteerwogen; A .gusiman-peileisi; A .beiqiao; I .E.makesi; (177 pag.)CN107531705; (2018); A;,
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The chemical industry reduces the impact on the environment during synthesis 6065-82-3, name is Ethyl diethoxyacetate, I believe this compound will play a more active role in future production and life. 6065-82-3

Example 1Synthesis of (Z)-2-ethoxy-3-{3′-[(methyloctanoylamino)methyl]biphenyl-4-yl}acrylic acid a-Ethyl Chloroethoxyacetate20 mL (112 mmol) of ethyl diethoxyacetate, 16 mL (224 mmol) of acetyl chloride and 60 mg (0.2 mmol) of iodine are placed in a round-bottomed flask and heated at 50 C. for 24 hours. The reaction progress is monitored by NMR. The excess acetyl chloride is removed by evaporation under vacuum. 19 g (100%) of ethyl chloroethoxyacetate are obtained in the form of a liquid colored brown by the residual iodine.; e-Ethyl Chloroethoxyacetate40 mL (224 mmol) of ethyl diethoxyacetate, 38 mL (536 mmol) of acetyl chloride and 0.11 g (0.45 mmol) of iodine are placed in a round-bottomed flask and heated at 50 C. for 24 hours. The reaction progress is monitored by NMR. The excess acetyl chloride is removed by evaporation under vacuum. 36.3 g (100%) of ethyl chloroethoxyacetate are obtained in the form of a liquid colored brown by the residual iodine.

The chemical industry reduces the impact on the environment during synthesis 6065-82-3. I believe this compound will play a more active role in future production and life.

Reference:
Patent; GALDERMA RESEARCH & DEVELOPMENT; US2009/12129; (2009); A1;,
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Adding some certain compound to certain chemical reactions, such as: 13831-03-3, name is tert-Butyl propiolate, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 13831-03-3. 13831-03-3

General procedure: A Schlenk tube (25 cm3) equipped with a magnetic stir barwas charged with terminal alkyne (1.2 mmol), (i-Pr)2EtN(1.5 mmol), CuBr¡¤SMe2 (0.1 mmol), TBPAc (0.3 mmol),oxirane (2.0 mmol), and 2.0 cm3 MeCN. After the mixturewas stirred at 25 C for 1 h, propiolate (1.0 mmol) wasadded under an inert atmosphere. The tube was evacuatedand backfilled with argon (three times). Subsequently, themixture was stirred for 16 h at appropriate temperature (seeTables 2, 3). After cooling to room temperature, the mixturewas passed through silica gel pad and concentrated underreduced pressure. The resulting residue was purified with column chromatography on silica gel (eluent gradient ofEtOAc/hexane, see spectroscopic analysis section) to givethe corresponding products 4 in the yields listed in Tables 2and 3.

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of tert-Butyl propiolate.

Reference:
Article; Jahanshad, Milad; Manafi, Mohammadreza; Mousavi-Safavi, Seyed Mahmoud; Homami, Seyed Saied; Ghazanfarpour-Darjani, Majid; Monatshefte fur Chemie; vol. 151; 1; (2020); p. 113 – 122;,
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In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 1128-76-3, name is Ethyl 3-chlorobenzoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. 1128-76-3

General procedure: A typical procedure is as follows. Magnesium turnings (0.36 g, 15 mmol) for Grignard reagent with no pre-treatment were placed in a 100 mL four-necked flask and were heated to dry. Carbon dioxide was introduced to the flask and a balloon filled with carbon dioxide was attached to the flask. Chlorotrimethylsilane (3.17 mL, 25 mmol) in dry DMF (30 mL) was added to the flask and the reaction mixture was stirred for 30 minutes at room temperature. Ethyl benzoate 1a (0.72 mL, 5 mmol) was added dropwise by means of a syringe and the reaction mixture was stirred at room temperature until the starting material disappeared. Then the reaction mixture was carefully poured into 1 M hydrochloric acid solution (100 mL) and the product was extracted with diethyl ether (40 mL) four times. The combined organic layer was washed with 1 M potassium carbonate solution (40 mL) twice and the product was transferred to the water layer. To the combined water layers, 3 M hydrochloric acid (200 mL) was added and the product was extracted with ether (40 mL) four times. The combined ether layer was washed with water (50 mL) and brine (50 mL), dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure to give the product 2a.

The synthetic route of 1128-76-3 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Maekawa, Hirofumi; Okawara, Hikaru; Murakami, Taro; Tetrahedron Letters; vol. 58; 3; (2017); p. 206 – 209;,
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In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 13671-00-6, name is Methyl 2,6-difluorobenzoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. 13671-00-6

To 30 ml of a THF solution containing 700 mg of 2-(2-chloropyridin-3-yl)acetic acid was added dropwise 7.75 ml of a 1.9 mol/L THF solution of hexamethyldisilazane sodium at -78 C. and the mixture was stirred for 10 minutes. Then, 616 mul of methyl 2,6-difluorobenzoate was added dropwise thereto, and then, the temperature of the mixture was raised from -78 C. to room temperature and stirred for 1 hour. To the mixture was added an aqueous saturated ammonium chloride solution followed by stirring the mixture for 1 hour. Thereafter, ethyl acetate was added thereto and the liquids were separated. The obtained organic layer was washed with saturated brine, and dried over sodium sulfate. After the solvent was distilled off under reduced pressure, the obtained residue was purified by silica gel column chromatography. The title compound was obtained as 450 mg of a transparent oily product. (1215) 1H-NMR (CDCl3) delta: 8.35 (1H, dd, J=4.7, 1.8 Hz), 7.66 (1H, dd, J=7.6, 1.8 Hz), 7.44-7.43 (1H, m), 7.25 (2H, dd, J=7.6, 4.7 Hz), 7.00-6.96 (2H, m).

The synthetic route of 13671-00-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MITSUI CHEMICALS AGRO, INC.; UMETANI, Hideki; OKAYA, Shun; IKISHIMA, Hideaki; FUKUMOTO, Takeshi; NISHIDA, Akihiro; YANAGI, Masanori; NAITO, Ryohei; MASUTOMI, Koji; SHIRAKAWA, Tomomi; SAKURADA, Akane; YUTANI, Satoshi; (368 pag.)US2020/45968; (2020); A1;,
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6933-47-7, Name is Methyl 4-amino-2-methylbenzoate, 6933-47-7, belongs to esters-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows.

A solution of 143 3,5-dichloro-4-ethoxybenzoic acid (7: R1=Et) (285mg, 1.21mmol) and 144 DIPEA (1.05mL, 6.05mmol) in 35 DMF (2.5mL) was added to 38 HATU (690mg, 1.82mmol) and the orange mixture was stirred for 5min prior to the addition of 145 methyl 4-amino-2-methylbenzoate (8: R=R2=Me) (200mg, 1.21mmol) in DMF (1mL). The resulting dark orange solution was stirred for 18h. 2M 117 HCl (10mL) was added and stirring continued for 10min, and then the mixture was extracted with diethyl ether. The organic layer was washed with water (3¡Á15mL), dried over MgSO4, filtered and the solvent was evaporated in vacuo. The yellow residue was purified by silica gel chromatography (40g, 0-100% 45 EtOAc in 136 isohexane) to afford 146 methyl 4-(3,5-dichloro-4-ethoxybenzamido)-2-methylbenzoate (10: R1=Et, R=R2=Me) (267mg, 56%): 1H NMR (400MHz, CDCl3) delta 7.97 (d, J=8.5Hz, 1H), 7.81 (2H, s), 7.83-7.77 (1H, m), 7.59-7.48 (2H, m), 4.18 (2H, q, J=7.0Hz), 3.89 (3H, s), 2.63 (3H, s), 1.49 (3H, t, J=7.0Hz). m/z 380 (M-H)- (ES-).

Statistics shows that Methyl 4-amino-2-methylbenzoate is playing an increasingly important role. we look forward to future research findings about 6933-47-7.

Reference:
Article; Clarke, Earl; Jarvis, Christopher I.; Goncalves, Maria B.; Kalindjian, S. Barret; Adams, David R.; Brown, Jane T.; Shiers, Jason J.; Taddei, David M.A.; Ravier, Elodie; Barlow, Stephanie; Miller, Iain; Smith, Vanessa; Borthwick, Alan D.; Corcoran, Jonathan P.T.; Bioorganic and Medicinal Chemistry; vol. 26; 4; (2018); p. 798 – 814;,
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Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 6962-92-1, name is 4-Chlorobutyl acetate, A new synthetic method of this compound is introduced below., 6962-92-1

To a suspension of sodium ethoxide (4 g, 59.18 mmol) in EtOM (50 mL) was added thiophenol (5 g, 45.45 mrnol) at0C, followed by drop-wise addition of 4-chiorobutyl acetate (7 g, 45.45 minol) over a period of 20 mm. and stirred the same temperature for 10 mm. and heated at reflux for 6 h. The RM was cooled the reaction to RT, added KOH pellets (2.6 g, 45.45 inmol), heated at reflux for4 h. After completion, the RM was poured into ice water, extracted with EtOAc (2 times), EtOAc layer was washed with water, brine, dried over anhydrous Na2SO4, filtered and the solvent was evaporated under reduced pressure to get crude compound. The crude compound was purified by silica gel(60-120 mesh) column chromatography, eluted with 8%EtOAc/pet ether to afford 4-(phenylthio)butan-1-ol as oily mass (6 g, 72%); ?H NMR (400 MHz, cdcl3) 5 7.33 (dd, J = 8.2,1.6 Hz, 2H), 7.30 – 7.23 (m, 2H), 7.20 – 7.14 (m, 1H), 3.65 (td, J = 5.0, 4.1, 3.0 Hz, 2H), 2.96 (t, J = 6.9 Hz, 2H),1.78 – 1.65 (m, 4H); Mass (M+H): 183, LCMS Purity: 99.83%.

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Patent; SUMITOMO CHEMICAL COMPANY, LIMITED; NAKASHIMA, Yosuke; JIN, Yoshinobu; WO2014/84407; (2014); A1;,
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