Month: March 2021

Some common heterocyclic compound, 5164-76-1, name is Dimethyl pent-2-enedioate, molecular formula is C7H10O4, 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. Application In Synthesis of Dimethyl pent-2-enedioate

General procedure: The crude aryl diazonium tosylate 9 thus obtained was dissolved or suspended in MeOH (30 mL). Dimethyl glutaconate (1.45 mL, 10.0 mmol) and Pd(OAc)2 (112 mg, 0.5 mmol) were successively added while stirring. After stirring at r.t. for 15 h, the mixture was concentrated under reduced pressure and partitioned between CH2Cl2 (40 mL) and H2O (25 mL). The organic layer was washed with brine, dried (Na2SO4), and concentrated in vacuo. The residue was briefly fractionated on SiO2 using CH2Cl2 or CH2Cl2- acetone (5:1) as eluent. Fractions containing arylation product were pooled and concentrated to give compound 10 of at least 90% purity (according to 1H NMR analysis). It was used in the next step without further purification.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5164-76-1, its application will become more common.

Reference:
Article; Dar’In, Dmitry; Kantin, Grigory; Bakulina, Olga; ?alubovskis, Raivis; Krasavin, Mikhail; Synthesis; vol. 51; 10; (2019); p. 2230 – 2236;,
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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. 145576-28-9, name is Ethyl 4-methylenecyclohexanecarboxylate, A new synthetic method of this compound is introduced below., COA of Formula: C10H16O2

At 0 C, to a solution of ethyl 4-methylenecyclohexanecarboxylate (0.08 g) in DCE (1 mL) was added chloroiodomethane (0.110 mL, 1.522 mmol), followed bythe addition of 1 N diethylzinc in hexane (0.76 1 mL, 0.76 1 mmol). The reaction was stirred at 0 C for 1 hr, then stirred at rt for 18 hrs. The reaction mixture was diluted with EtOAc and 1 N HC1, the organic phase was washed with sat. NaC1, dried over anhydrous Na2SO4, filtered and concentrated. The crude product was charged to a 25 g silica gel cartridge which was eluted with a 20 mm gradient of 0-6% EtOAc inhexane to yield ethyl spiro[2.5]octane-6-carboxylate. ?H NMR (400 MHz, CDC13) ppm 4.08-4.18(2 H, m), 2.32 (1 H, tq, J=11.01, 3.53 Hz), 1.85 – 1.93 (2 H, m), 1.53- 1.74 (4 H, m), 1.28 – 1.35 (2 H, m), 1.22 – 1.28 (3 H, m), 0.28 (2 H, ddd, J=8.53, 5.52, 1.51 Hz), 0.17 – 0.25 (2 H, m).

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; BRISTOL-MYERS SQUIBB COMPANY; HEWAWASAM, Piyasena; LOPEZ, Omar D.; TU, Yong; WANG, Alan Xiangdong; XU, Ningning; KADOW, John F.; MEANWELL, Nicholas A.; GUPTA, Samayamunthula Venkata Satya Arun Kumar; KUMAR, Indasi J. Gopi; PUNUGUPATI, Suresh Kumar; BELEMA, Makonen; WO2015/5901; (2015); A1;,
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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. 457097-93-7, name is Methyl 4-amino-3-(trifluoromethoxy)benzoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Recommanded Product: 457097-93-7

To a 500 mL round-bottom flask was added methyl 4-amino-3- (trifluorornethoxy)benzoate (7.1 g, 30.19 mmol, 1.0 equiv.), AcOH (100 mL), and NaSCN (12.1 g, 149.25 mmol, 5.0 equiv.) followed by the dropwise addition of bromine (9.6 g, 60.07 mmol, 2.0 equiv.) in AcOH (50 mL) at 0 C over a 1 h. The mixture was stirred at 0 C for 2 h, and then at 40 C overnight. The reaction mixture was again cooled to 0 C, and NaSCN (12.2 g, 150.49 mmol, 5.0 equiv.) was added, followed by the dropwise addition of bromine (9.6 g, 60.07 mmol, 2.0 equiv.) in AcOH (50 mL) over a 1 hr period. The reaction mixture was stirred at 0 C for 2 h, then at 40 C for 3 days. The resulting mixture was diluted with water (200 mL) and the pH value of the solution was adjusted to 9 using sodium hydroxide. The resulting solids were collected by filtration, washed with water (20 ml x 2), and dried in an oven at 60 C for 6 h to provide methyl 2-amino-4-(trifluoromethoxy)-l,3-benzothiazole-6-carboxylate A4b (5.4 g, 61%) as a brown solid.

The synthetic route of 457097-93-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ARDELYX, INC.; CHAO, Jianhua; JAIN, Rakesh; HU, Lily; LEWIS, Jason Gustaf; BARIBAULT, Helene; CALDWELL, Jeremy; (249 pag.)WO2018/39384; (2018); A1;,
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Reference of 75567-84-9,Some common heterocyclic compound, 75567-84-9, name is Methyl 3-(4-bromophenyl)propanoate, molecular formula is C10H11BrO2, 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.

Methyl 3-(4-bromophenyl)propanoate (1a) (1.0 g, 4.11 mmol) was dissolved in 7mL ofN,N?-dimethylformamide (DMF). Copper (I) iodide (156 mg, 0.82 mmol),triethylamine (TEA 1.2mL, 8.23mmol), tetrakis (triphenylphosphine) palladium (0)Pd(PPh3)4 475 mg, 0.41 mmol, trimethylsilylacetylene (TMSA 0.74 mL, 5.35mmol) were added and the reaction mixture was stirred at 80 C under Ar until all thestarting material was consumed, as was monitored by TLC. The reaction mixture wasfiltered through a pad of celite and organic solvent (ethyl acetate: n-hexane = 10:1) wasadded. The organic phase was washed two times with saturated ammonium chloride,brine and then dried over magnesium sulfate. The solvent was evaporated to yield theproduct 740 mg and it was used to next without further purification.

The synthetic route of 75567-84-9 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Ebara, Yasuhito; Hayashi, Tenko; Hori, Sakiko; Kaihatsu, Kunihiro; Kato, Nobuo; Ogata, Katsuya; Okazaki, Miku; Sawada, Shinjiro; Takagi, Kenji; Molecules; vol. 25; 4; (2020);,
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Related Products of 21961-31-9, These common heterocyclic compound, 21961-31-9, name is Methyl 3-amino-5-chlorobenzoate, 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.

3-Amino-5-chloro-benzoic acid methyl ester (CAS 21961-31-9, 0.400 g) was dissolved in 10.5 ml of chloroform and treated at 0 C with 0.344 g of isobutyryl chloride (1.5 eq.) and 0.90 ml of triethylamine. After stirring for 2 h at ambient temperature, the reaction mixture was poured onto crashed ice/HCl-solution, extracted twice with AcOEt, washed with water, dried over sodium sulfate, and evaporated i. V. Flash chromatography (Si02, hexane/AcOEt=7/3) yielded finally 0.546 g of pure 3-chloro-5-isobutyrylamino-benzoic acid methyl ester as white waxy solid. MS 256.0 ([M+H]+). It was dissolved in 12.8 ml of THF/EtOH =1/1, treated with 6.4 ml (3 eq.) of IN NaOH and kept at ambient temperature for 2 h. The reaction mixture was then poured onto crashed ice/AcOEt/HCl dil., the aqueous phase extracted again with AcOEt, the combined organic layers were washed with water, dried over sodium sulfate, and evaporated to dryness to produce 0.529 g of 3-chloro-5-isobutyrylamino-benzoic acid as white solid. MS 240.1 ([M-H]”).

Statistics shows that Methyl 3-amino-5-chlorobenzoate is playing an increasingly important role. we look forward to future research findings about 21961-31-9.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; WO2006/27135; (2006); 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 141-12-8 as follows. Product Details of 141-12-8

6.983g (0.035mol) of 1a was added to a stirring solution of 0.491g (3.5mmol) of salicylic acid, 0.665g (3.5mmol) of SeO2 and 14.82g (0.164mol) of tert-butylhydroperoxide (70%) in 35mL of diethyl ether at 0C and left to stir for 48h. The volume of the mixture was then reduced to one half and was washed with 15mL of 5% NaHCO3, saturated CuSO4, repeatedly washed with saturated Na2S2O3, water, brine and then dried over MgSO4. Solvent was removed by rotary evaporation and the crude oil was then purified by flash chromatography (5% EtOAc/hexanes) to afford 3.53g (47%) of 2a. TLC: (Rf 0.7). 1H NMR (300MHz): delta 9.28 (s, 1H), 6.37 (t, 1H), 5.32 (t, 1H), 4.49 (d, 2H), 2.39 (q, 2H), 2.25 (t, 2H), 1.91 (s, 3H) 1.69 (s, 3H), 1.58 (s, 3H). 13C NMR (76MHz): delta 195.2, 171.0, 153.2, 140.8, 139.7, 120.5, 60.7, 30.4, 27.3, 25.8 (contaminant), 23.2, 21.0, 9.2.

According to the analysis of related databases, 141-12-8, the application of this compound in the production field has become more and more popular.

Reference:
Article; Mostafavi, Anahita Z.; Lujan, Donovan K.; Erickson, Katelyn M.; Martinez, Christina D.; Troutman, Jerry M.; Bioorganic and Medicinal Chemistry; vol. 21; 17; (2013); p. 5428 – 5435;,
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Reference of 443-26-5, 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. 443-26-5, name is Ethyl 2-fluorobenzoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

5,6-Dihydro-cyclopenta[b]thiophen-4-one (2.1 g, 15.0 mmol) in 15 mL of THF was treated with NaH (60 percent, 1.5 g, 36 mmol). After the addition of 3-Fluoro-benzoic acid ethyl ester, the reaction mixture was heated at 100 C. for 8 hr. The solution was cooled to room temperature and poured into water. The resulting mixture was acidified with concentrated HCl and was added with ethyl acetate (70 mL). The organic layer was collected, brined, dried over MgSO4(s), and concentrated under reduced pressure. The resultant precipitate was collected and recrystallized from ethanol to provide the corresponding 5-(2-Fluoro-benzoyl)-5,6-dihydro-cyclopenta[b]thiophen-4-one (0.56 g, 2.1 mmol) as brown solid in 14% yield.

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, Ethyl 2-fluorobenzoate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; DEVELOPMENT CENTER FOR BIOTECHNOLOGY; LIAO, Chu-Bin; CHIANG, Chao-Cheng; YANG, Huei-Ru; LIAO, Yuan-Chun; CHEN, Paonien; US2013/274255; (2013); A1;,
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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. 924-99-2, name is Ethyl 3-(dimethylamino)acrylate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Quality Control of Ethyl 3-(dimethylamino)acrylate

General procedure: Ethyl 4-(4-chlorophenyl)-2-thioxo-1,2,3,4-tertahydropyrimidine-5-carboxylate 6a (Table 2, entry 1). To a mixture of thiourea 12a (23.0 mg, 0.302 mmol), 4-chlorobenzaldehyde 13a (63.0 mg, 0.448 mmol), and ethyl 3-dimethylaminoacrylate 9 (64.0 mg, 0.447 mmol) in anhydrous DMF (0.3 mL) was added anhydrous aluminum chloride (8.0 mg, 0.0600 mmol) at room temperature, and the reaction mixture was stirred at 110 C for 3 h. To the mixture was added EtOAc (10 mL) and 1 M HCl aqueous solution (5 mL), and the organic layer was separated. The aqueous layer was extracted with EtOAc (10 mL), and the combined organic layers were washed with water (5 mL) and brine (5 mL), dried over anhydrous MgSO4, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography [n-hexane-EtOAc (4:1 to 2:1)] to give 6a (78.9 mg, 0.266 mmol, 88%) as pale yellow crystals.

The synthetic route of 924-99-2 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Arai, Rie; Cho, Hidetsura; Gokurakuji, Yuki; Kikuchi, Hidetomo; Kubo, Takanori; Nakamura, Yuri; Nishimura, Yoshio; Sunaga, Katsuyoshi; Yuan, Bo; Tetrahedron Letters; (2020);,
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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 4224-69-5 as follows. name: Methyl 2-(bromomethyl)acrylate

General procedure: A mixture of (E)-3-phenyl-2-[(toluene-4-sulfonylamino)methyl]-acrylic acid methyl ester (345 mg, 1.0 mmol), methyl 2-(bromomethyl)acrylate (269 mg, 1.5 mmol), and K2CO3(276 mg, 2.0 equiv) in DMF (3.0 mL) was stirred at room temperature for 5 h. After removal of the solvent and column chromatographic purification process (hexanes/Et2O, 5:1) compound 1a was obtained as a white solid, 401 mg (90%). Other compounds 1b-m were prepared analogously, and the spectroscopic data of 1a-m are as follows.

According to the analysis of related databases, 4224-69-5, the application of this compound in the production field has become more and more popular.

Reference:
Article; Kim, Ko Hoon; Lim, Jin Woo; Moon, Hye Ran; Kim, Jae Nyoung; Bulletin of the Korean Chemical Society; vol. 35; 11; (2014); p. 3254 – 3260;,
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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. 680-65-9, name is Diethyl difluoromalonate, A new synthetic method of this compound is introduced below., SDS of cas: 680-65-9

Diethyl difluoropropanedioate (2.87 ml, 17.23 mmol) was dissolved in MeOH (20 mL) and a solution of 2,3-dihvdro-1H-inden-2-ainine (2.07 g, 15.51 mmol) in MeOH (15mL) was added dropwise. The reaction was stirred at RT for 14 h. The reaction wasconcentrated and purified by Biotage FCC (50 g SNAP KP-Si02, 0-50% EtOAc in Heptanes)affording the title compound as a pale brown solid (1.79 g, 91% purity, 35%)?H NMR (500 MHz, DMSO-d6) 9.48 (d, J = 6.9 Hz, 1H), 7.22 (dcl, J = 5.3, 3.4 Hz,2H), 7.15 (dd, J = 5.5, 3.2 Hz, 2H), 4.60-4.48 (in, IH). 3.88 (s, 3H), 3.20 (dd, .J= 15.9, 7.9Hz, 2H), 2.91 (dd, J= 15.9, 6.6 Hz, 2H). LCMS Method C: rt 1.09 mm, 91%, m/z 269.95(MW)

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; PRESIDENT AND FELLOWS OF HARVARD COLLEGE; EVOTEC INTERNATIONAL GMBH; GAMPE, Christian, M.; KAHNE, Daniel, Evan; KAHNE, Suzanne, Walker; QIAO, Yuan; EAST, Stephen; PARKES, Alastair, L.; SOUTHEY, Michelle; HUNTER, James; WHITTAKER, Mark; ARTHUIS, Martin; (359 pag.)WO2016/191658; (2016); A1;,
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