Month: November 2020

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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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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These common heterocyclic compound, 148547-19-7, name is Methyl 4-bromo-3-methylbenzoate, 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. 148547-19-7

A suspension of methyl 4-bromo-3-methylbenzoate (ABCR AV19078; 15 g; 65.48 mmol; 1 eq.), o-tolylboronic acid (Aldrich 393606; 10.68 g; 78.5 mmol; 1.2 eq.), potassium carbonate (45.25 g, 327.4 mmol, 5 eq.) and tetrakis(triphenylphosphine)palladium(0) (3.78 g; 3.27 mmol; 0.05 eq.) in toluene (200 ml_) and water (200 ml_) was stirred at 12O0C for 6 hours. The resulting mixture was allowed to return to room temperature and the two phases were separated. The organic layer was concentrated in vacuo and purified by column chromatography (c-hexane) to afford the title compound (15 g, 95%) as a white solid.HPLC (Method B) : Rt 3.01 min (purity 98.7%). 1H NMR (DMSOd6, 400MHz) delta 7.91 (1 H, s), 7.83-7.81 (1 H, m), 7.33-7.30 (2H, m), 7.28-7.26 (1 H, m), 7.25-7.22 (1 H, m), 7.07-7.05 (1 H, d), 3.86-3.81 (3H, s), 2.09-2.00 (3H, s), 1.97-1.92 (3H, s).

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 148547-19-7.

Reference:
Patent; MERCK SERONO S.A.; WO2009/43890; (2009); 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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23877-12-5, Adding some certain compound to certain chemical reactions, such as: 23877-12-5, name is tert-Butyl 2-bromo-2-methylpropanoate, 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 23877-12-5.

2-Methyl-2-{4-[3-(4-trifluoromethyl-phenyl)-[1,2,4]thiadiazol-5-ylmethylsulfanyl]-phenoxy}-propionic acid tert-butyl ester To a three-necked flask containing NaH (36 mg, 0.90 mmol; 60% in mineral oil) was added a solution of B1 (220 mg, 0.598 mmol) in THF. To the mixture at 40 C. was added tert-butyl 2-bromoisobutyrate (287 mg, 1.29 mmol). After heating at 70 C. for 2 h, more tert-butyl 2-bromoisobutyrate (215 mg, 0.970 mmol) was added and the heating was continued overnight. The mixture was quenched with water (0.1 mL), concentrated, and chromatographed (EtOAc/hexane) to give 81 mg (27%) of B2; 1H NMR (300 MHz, CDCl3) delta 8.35 (d, J=8.2 Hz, 2 H), 7.71 (d, J=8.2 Hz, 2 H), 7.34 (d, J=8.8 Hz, 2 H), 6.78 (d, J=8.7 Hz, 2 H), 4.42 (s, 2 H), 1.55 (s, 6 H), 1.38 (s, 9 H); MS (ES) m/z: 511 (M+H+).

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 23877-12-5.

Reference:
Patent; Kuo, Gee-Hong; Shen, Lan; Wang, Aihua; Zhang, Yan; US2005/96362; (2005); A1;,
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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 148547-19-7 as follows. 148547-19-7

Step A. Methyl 2,2′-dimethyl-1,1′-biphenyl-4-carboxylate A mixture of methyl 4-bromo-3-methylbenzoate (25.0 g, 110 mmol), o-tolylboronic acid (16.5 g, 120 mmol) and potassium carbonate (50 g, 360 mmol) in dioxane/water (300 mL:200 mL) was purged with nitrogen for 1 hour. [1,-bis(Diphenylphosphino) ferrocene]dichloropalladium [II] (4.5 g, 5.5 mmol) was added. The reaction mixture was heated to 100 C. with vigorous stirring for 3.5 hours, then cooled and filtered through Celitee (Celite Corp., Santa Barbara, Calif.). The cake was washed with ethyl acetate (500 mL). The combined organic phases were washed with 1N sodium hydroxide (500 mL) and brine (500 mL), dried over anhydrous potassium carbonate, and concentrated in vacuo to afford a dark oil (28.6 g). Purification by flash chromatography using 2% ethyl acetate in hexanes as solvent provided the title compound (24.7 g, 93%) as a pale yellow oil. MS [(+)ESI, m/z]: 241 [M+H]+ HRMS [(+)ESI, m/z]: 241.12205 [M+H]+. Calcd for C16H17O2: 241.12286 Anal. Calcd for C16H16O2: C, 79.97; H, 6.71. Found: C, 79.67; H, 6.61.

According to the analysis of related databases, 148547-19-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Wyeth; US2006/199806; (2006); A1;,
Ester – Wikipedia,
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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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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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110661-91-1, These common heterocyclic compound, 110661-91-1, name is tert-Butyl 4-bromobutanoate, 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.

Step 2: Preparation of tert-butyl 4-(2-formyl-5-(trifluoromethyl)phenoxy)butanoate A flask was charged with 2-hydroxy-4-(trifluoromethyl)benzaldehyde (300 mg, 1.58 mmol, 1.00 equiv), DMF (10 mL), potassium carbonate (654 mg, 4.73 mmol, 3.00 equiv), and tert-butyl 4-bromobutanoate (702 mg, 3.15 mmol, 2.00 equiv). The resulting solution was stirred overnight at 100 C. and quenched with water (30 mL). The resulting solution was extracted with DCM (2*50 mL) and the organic layers were combined, washed with brine (2*30 mL), dried over anhydrous sodium sulfate, filtered and concentrated. The residue was chromatographed on a silica gel column with EtOAc/petroleum ether (1/10) to provide 450 mg (86% yield) of tert-butyl 4-(2-formyl-5-(trifluoromethyl)phenoxy)butanoate as a light yellow solid. 1H NMR (300 MHz, Chloroform-d) delta 10.5 (s, 1H), 7.96 (d, J=7.5 Hz, 1H), 7.29-7.33 (m, 2H), 4.22 (t, J=6.0 Hz, 2H), 2.50 (t, J=6.0 Hz, 2H), 2.18-2.25 (m, 2H), 1.49 (s, 9H).

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 110661-91-1.

Reference:
Patent; ABIDE THERAPEUTICS, INC.; GRICE, Cheryl A.; BUZARD, Daniel J.; SHAGHAFI, Michael B.; (108 pag.)US2018/134674; (2018); A1;,
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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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