Month: August 2021

These common heterocyclic compound, 57486-68-7, name is Methyl 2-chlorophenylacetate, 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. category: esters-buliding-blocks

EXAMPLE 35 Preparation of 1-(o-Chlorophenyl)-3-azabicyclo[3.1.0]hexane hydrochloride A stirred mixture of 36.9 g of methyl o-chlorophenylacetate, 36.0 g of N-bromosuccinimide, and 2 drops of 48% hydrobromic acid in 500 ml of carbon tetrachloride is refluxed for 20 hours and then filtered through magnesium silicate. Evaporation under reduced pressure gives methyl alpha-bromo-o-chlorophenylacetate as a straw-colored liquid.

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

Reference:
Patent; American Cyanamid Company; US4131611; (1978); A;,
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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. 18469-52-8, name is Methyl 4-(aminomethyl)benzoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. SDS of cas: 18469-52-8

A solution of methyl 4-(aminomethyl)benzoate (2.000 g, 9.918 mmol), morpholine- 4-carbonyl chloride ( 1.635 g, 10.910 mmol) and N,N-diisopropylethylamine (5.183 mL, 29.755 mmol) in dichloromethane (20 mL) was stirred at the room temperature for 12 hr. The reaction mixture was concentrated under the reduced pressure to remove the solvent, and water was added to the concentrate, followed by extraction with dichloromethane. The organic layer was washed with aqueous saturated sodium chloride solution, dried (anhydrous MgS04), filtered, and concentrated in vacuo. The concentrate was purified and concentrated by column chromatography (SiO:, 12 g cartridge; ethyl acetate / hexane = 0 % to 50 %) to give the title compound methyl 4-((morpholine-4-carboxamido)methyl)benzoate as White solid (2.200 g. 79.7 %).

The synthetic route of 18469-52-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CHONG KUN DANG PHARMACEUTICAL CORP.; LEE, Jaekwang; KIM, Yuntae; LEE, Chang Sik; SONG, Hyeseung; GWAK, Dal-Yong; LEE, Jaeyoung; OH, Jung Taek; LEE, Chang Gon; KIM, II Hyang; (1041 pag.)WO2017/23133; (2017); A2;,
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Reference of 40061-54-9, 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 40061-54-9 as follows.

Step 4. DBU (4.1 g, 26.9 mmol, 1.2 eq) was added to a mixture of 4-(methylamino)-2-(methylthio)-pyrimidine-5-carbaldehyde (4.1 g, 22.4 mmol, 1.0 eq) and ethyl 2-(2-chlorophenyl)acetate (5.4 g, 26.9 mmol, 1.2 eq) at RT. The resulting mixture was then stirred at room temperature for 1 h, followed by addition of water and extraction with EtOAc. The combined organic layers were dried and concentrated to afford 6-(2-chlorophenyl)-8-methyl-2-(methylthio)pyrido[2,3-d]pyrimidin-7(8H)-one (5.0 g, 70percent in yield).

According to the analysis of related databases, 40061-54-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Taunton, JR., John William; Brameld, Kenneth Albert; Goldstein, David Michael; Mcfarland, Jesse; Krishnan, Shyam; Choy, Jonathan; US2014/323464; (2014); A1;,
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These common heterocyclic compound, 2318-25-4, name is Ethyl 3-ethoxy-3-iminopropionate hydrochloride, 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. HPLC of Formula: C7H14ClNO3

A solution of 1, 2-phenylenediamine (1.0 equivalent) and ethyl 3- ETHOXY-3-IMINOPROPANOATE hydrochloride (1.3 equivalents) in ethanol was stirred at 90 C overnight. The reaction was cooled to room temperature and the solvent was removed in vacuo. Water and CH2CI2 were added to the residue. The organic layer was separated, dried over NA2SO4 and the solvent removed. The solid recovered was used without purification. LC/MS M/Z 205.2 (MH+), RIF 1. 44 minutes.

The synthetic route of Ethyl 3-ethoxy-3-iminopropionate hydrochloride has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CHIRON CORPORATION; WO2004/18419; (2004); A2;,
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Adding a certain compound to certain chemical reactions, such as: 25597-16-4, name is Ethyl 4,4,4-trifluorocrotonate, belongs to esters-buliding-blocks compound, 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 25597-16-4, SDS of cas: 25597-16-4

[0319] A mixture of 4-benzyl-2-hydroxy-3-methylbenzaldehyde prepared as in Step 4 (1.07 g, 4.73 mmole), K2C03 (0.654 g, 4.73 mmole) and ethyl 444-trifluocrotonate (484 uL, 5.67 mmole) in anhydrous DMF (5.0 mL) was heated to 85 C under a dry N2 atmosphere for 2.75 h. The mixture was then cooled, poured into IN HC1 (100 ml) and extracted with EtOAc (2 X 100 mL). The combined extracts were washed with brine (100 mL), dried over MGS04, filtered and concentrated in vacuo to give 1.86 g of a yellow oil. The crude product was purified by silica chromatography (95: 5 hexanes: EtOAc) to give 1.04 g (59% yield) of the product as a light yellow oil: EIHRMS NILZ 376. 1310 (M+, C21H19F3O3, Calc’d 376.1286).

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 4,4,4-trifluorocrotonate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; PHARMACIA CORPORATION; WO2004/87686; (2004); A2;; ; Patent; PHARMACIA CORPORATION; WO2004/87687; (2004); A1;,
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Reference of 609-12-1,Some common heterocyclic compound, 609-12-1, name is Ethyl 2-bromo-3-methylbutanoate, molecular formula is C7H13BrO2, 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.

52.4 g of activated zinc powder and 450 ml of anhydrous THF,Add a few drops under N2 protectionEthyl alpha-bromoisovalerate2 to trigger the reaction,66 reflux 45min stirring until the reaction liquid becomes dark green after adding 20.324g (0.165mol)Cyclohexyl acetonitrile,And slowly add 2 (88.71 g, 0.4243 mol) within 1 h,Continue to reflow 1H stop heating, cooled to room temperature,Add 80ml 50% K2CO3 solution was stirred vigorously for 10min, the reaction solution was allowed to stratification, the organic phase was separated, the residue was extracted with THF,The combined organic phases were hydrolyzed by adding 150 ml of 15% HCl, the organic layer was separated and concentrated under reduced pressure, the aqueous layer was extracted three times with ethyl acetate,The combined organic phases were washed three times with saturated sodium bicarbonate solution, saturated NaCl, dried over anhydrous Na2SO4,The solvent was removed under reduced pressure to give compound 3 as a crude reddish brown liquid, 38.4 g, which was used directly in the next reaction without purification.

The synthetic route of 609-12-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Yunnan University; Chinese Academy Of Sciences Kunming Animal Institute; He Yanping; Zheng Yongtang; Zhang Yufang; Xiang Siying; Zhang Hongbin; Zhao Zhidong; Yang Liumeng; (9 pag.)CN106866548; (2017); A;,
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Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 139102-34-4, name is Methyl 4-bromo-2-methoxybenzoate, This compound has unique chemical properties. The synthetic route is as follows., Computed Properties of C9H9BrO3

General procedure: To 2 dram, stir-bar equipped vials, were added the aryl bromides (1.0 equiv). A stock solution of Ir[dF(CF3)ppy]2(dtbbpy)PF6 (1.0 mol%) and carboxylic acid 5 (1.1 equiv) in DMF (0.15 M with respect to carboxylic acid 5) was prepared, and to this stock solution was added TMG (1.1 equiv). The resulting stock solution was kept under a blanket of nitrogen. A separate solution of [Ni(dtbbpy)(H2O)4]Cl2 (10 mol%) in DMF (0.04 M) was prepared. The stock solution of Ir cat./acid/TMG was added to the aryl bromide monomers, followed by the Ni stock solution. The reaction mixtures were purged by blowing nitrogen over the top, sealed, and irradiated with blue LED (34 W LED Kessil lamps) for 24 h at room temperature. The reaction mixtures were diluted with EtOAc (3 mL) and H2O (4 mL). The organic layer was separated and concentrated under reduced pressure. The resulting residue was purified by silica gel chromatography with a solvent gradient from 0%EtOAc/hexanes to 100% EtOAc/hexanes to deliver the title compound.

According to the analysis of related databases, 139102-34-4, the application of this compound in the production field has become more and more popular.

Reference:
Article; Suen, Linda M.; Wang, Cheng; Hunter, David N.; Mitchell, Helen J.; Converso, Antonella; Elmarrouni, Abdellatif; Synthesis; vol. 50; 16; (2018); p. 3177 – 3186;,
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Electric Literature of 89-91-8, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 89-91-8 name is Methyl 2,2-dimethoxyacetate, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

Lithium hexamethyldisilane (55 mL of a 1 .OM solution in tetrahydrofuran, 55mmoles) was added to a solution of 3-acetylpyridine (5.5 mL, 50 mmoles), methyl dimethoxy acetate (6.7 mL, 55 mmoles) and anhydrous tetrahydrofuran (100 mL) with cooling at -45 C. The resulting reaction mixture was allowed to warm to 25 C over 1 hour, and stirred at this temperature for 3 hours. The reaction mixture was then concentrated under reduced pressure, and the residue was suspended in methanol (50 mL) andconcentrated under reduced pressure. The resulting residue was suspended in methanol (150 mL) and treated with hydrazine monohydrate (2.62 mL, 55 mmoles) and glacial acetic acid (6.29 mL, 110 mmoles), and the reaction mixture was heated at reflux for 14 hours. The resulting reaction mixture was cooled to 25 C and concentrated under reduced pressure. The residue was partitioned between ethyl acetate (200 mL) and iN aqueous sodiumhydroxide solution (100 mL). The layers were separated, and the organic layer was washed successively with iN aqueous sodium hydroxide solution (50 mL) and brine (50 mL), dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to yield 8.83 g of the title compound as a beige solid. 1H NMR (CDC13): oe 10.5 (br s, 1H) 9.03 (d, 1H), 8.57 (dd, 1H), 8.09 (dt, 1H), 7.34(dd, 1H), 6.65 (s, 1H), 5.63 (s, 1H), 3.39 (s, 6H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Methyl 2,2-dimethoxyacetate, and friends who are interested can also refer to it.

Reference:
Patent; E. I. DU PONT DE NEMOURS AND COMPANY; CLARK, David, Alan; FRAGA, Breena, Gloriana; ZHANG, Wenming; WO2015/38503; (2015); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 14062-30-7, name is Ethyl 2-(3-bromophenyl)acetate, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: Ethyl 2-(3-bromophenyl)acetate

Method A (3-Cyano-phenyl)-acetic acid ethyl ester To a mixture of of (3-bromo-phenyl)-acetic acid ethyl ester (15.3 g, 62.9 mmol) and 1-methyl-2-pyrrolidinone (125 mL) was added copper (I) cyanide (8.46 g, 94.4 mmol). The reaction mixture was stirred in an oil bath at 190 C. for 1 h. The reaction was cooled to room temperature and was diluted with EtOAc and 2:1 H2O/NH4OH. The mixture was stirred for 10 minutes and was filtered through Celite. The aqueous layer was washed with EtOAc (2*). The organic solution was washed with 2:1 H2O/NH4OH until the aqueous extracts were no longer blue. The organic solution was dried over MgSO4, filtered and concentrated to afford (3-cyano-phenyl)-acetic acid ethyl ester (11.95 g). 1H NMR (400 MHz, CDCl3) delta7.51-7.58 (m, 3H), 7.43 (t, 1H), 4.16 (q, 2H), 3.63 (s, 2H), 1.25 (t, 3H).

According to the analysis of related databases, 14062-30-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Pfizer Inc.; US6344485; (2002); B1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

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 13195-64-7 as follows. HPLC of Formula: C9H16O4

General procedure: At room temperature, to a solution of nitroalkenes 2 (0.2 mmol) and chiral catalyst Q4 or QD4 in THF was added dimethyl malonate 3 (68 muL, 0.3 mmol). The resulting mixture was purified by flash chromatography when 2 was consumed through a TLC analysis to afford the product 4 or 5.

According to the analysis of related databases, 13195-64-7, the application of this compound in the production field has become more and more popular.

Reference:
Article; Li, Fei; Li, Ying-Zi; Jia, Zhen-Shan; Xu, Ming-Hua; Tian, Ping; Lin, Guo-Qiang; Tetrahedron; vol. 67; 52; (2011); p. 10186 – 10194;,
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Ester – an overview | ScienceDirect Topics