Esters-buliding-blocks

Some common heterocyclic compound, 57381-43-8, name is Methyl 2,5-dibromobenzoate, molecular formula is C8H6Br2O2, 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. 57381-43-8

General procedure: A mixture of magnesium turnings (0.036g, 1.5mmol), bromobenzene (0.15g, 1mmol), tri-n-butyltin chloride (0.49g, 1.5mmol) and 1,2-dibromoethane (0.094g, 0.5mmol) as initiator in dry THF (5mL) was sonicated for 1h in an ultrasonic cleaning bath at around 35¡ãC, with monitoring of the reaction by TLC. Once the reaction finished, aqueous saturated NH4Cl solution (40mL) was added and extracted with ethyl acetate (3¡Á20mL). The combined extracts were washed with brine (60mL) and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure and the product was isolated by column chromatography with silica gel doped with 10percent of KF to retain tri-n-butyltin halides formed during the reaction. 4 (0.286, 0.78mmol, 78percent) eluted with 98:2 (hexane/diethyl ether).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 57381-43-8, its application will become more common.

Reference:
Article; Gerbino, Dario C.; Fidelibus, Pablo M.; Mandolesi, Sandra D.; Ocampo, Romina A.; Scoccia, Jimena; Podesta, Julio C.; Journal of Organometallic Chemistry; vol. 741-742; 1; (2013); p. 24 – 32;,
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455-75-4, These common heterocyclic compound, 455-75-4, name is Ethyl 3-amino-4-fluorobenzoate, 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 Ethyl 4-fluoro-3-methoxyacetamido-benzoate A solution of 2.8 g (15.3 mMol) of ethyl 3-amino-4-fluoro-benzoate (cf. L. S. Fosdick, A. F. Dodds in J. Amer. Chem. Soc. 65, 2305 (1943)) and 1.56 ml (1.85 g=17.0 mMol) of methoxyacetylchloride in 50 ml chlorobenzene was stirred for 1 hour at 50 C. and then refluxed for 15 minutes. Then the solvent was distilled off in vacuo and the crude product obtained was purified by flash chromatography (silica gel; dichloromethane/ethanol=100:1). The desired compound, initially oily, solidified within a few days. Yield: 3.8 g (98% of theory), Rf value: 0.38 (silica gel; dichloromethane/ethanol=19:1)

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 455-75-4.

Reference:
Patent; Boehringer Ingelheim Pharma KG; US6087380; (2000); A;,
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178312-47-5, 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. 178312-47-5, name is Ethyl 4,4-difluorocyclohexanecarboxylate, A new synthetic method of this compound is introduced below.

.4.4-Difluorocyclohexanecarbaldehvde; )-Propylmagnesium chloride (20 mL of a 2.0 M solution in THF, 40 mmol) was added dropwise to a oled (-150C) suspension of ethyl-4,4-difluorocyclohexanecarboxylate (3.0 g, 15.6 mmol) and N1O- nethylhydroxylamine hydrochloride (2.28 g, 23.4 mmol) in THF (30 mL). The reaction mixture was rred for 15 min then quenched with satd. NuH4Cl(aq). The product was extracted into ethyl acetate 2). The combined organic extracts were washed with brine, dried (MgSO4) and concentrated to give i-difluoro-iV-methoxy-N-methylcyclohexanecarboxamide as a clear oil (3.01 g, 93% yield). ? a solution of the aforementioned Wei?reb amide (3.0 g, 14.5 mmol) in diethyl ether (30 mL) at -780C is added, dropwise, diisobutylaluminium hydride (16 mL of a 1.0 M solution in toluene).On mpletion of addition, the mixture was stirred for a further 15 min before being poured into a stirred xture of diethyl ether (50 mL), hexanes (50 mL) and IN HCl(aq) (100 mL). The mixture was stirred r 5 rnins and then the layers were separated and the organic phase dried (MgSO4) and concentrated to /e 4)4-difluorocyclohexanecarboxaldehyde.

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; MERCK SHARP & DOHME LIMITED; WO2006/134341; (2006); A1;,
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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. 1186-73-8, name is Trimethyl methanetricarboxylate, A new synthetic method of this compound is introduced below., 1186-73-8

Step 6; methyl 10-(((tert-butyldimethylsilyl)oxy)methyl)-l-(2,4-dimethoxybenzyl)-4- hydroxy-9-methyl-2-oxo-l,2,5,6,7,9-hexahydropyrido[3′,2′:6,7]cyclohepta[l,2- f] indole-3-carboxylate Crude N-(2-((tert-butyldimethylsilyloxy)methyl)-l-methyl-6,7,8,9- tetrahydrocyclohepta[fJindol-5(lH)-ylidene)-l-(2,4-dimethoxyphenyl)methanamine (10.6 g, 20.91 mmol) and trimethyl methanetricarboxylate (6.80 g, 35.76 mmol) were mixed together in PI12O (40 mL). With stirring, the mixture was placed onto a pre-heated heat block at 230 C and heated for 10 min after the initial bubbling of MeOH was observed (occurs at -160 C internal reaction temperature). The reaction mixture was cooled to room temperature, then purified by column chromatography (hexanes followed by EtOAc/hexanes 0-80% gradient) to yield the product as a yellow foam (7.44 g, 56%, 2 steps). XH NMR (500 MHz, CHCl3-i/) delta ppm 0.08 (s, 3 H) 0.09 (s, 3 H) 0.90 (s, 9 H) 1.45 – 1.55 (m, 1 H) 1.85 – 1.95 (m, 1 H) 1.96 – 2.05 (m, 1 H) 2.32 – 2.44 (m, 1 H) 2.58 (dd, J=13.4, 6.1 Hz, 1 H) 2.96 (dd, J=13.4, 5.4 Hz, 1 H) 3.33 (s, 3 H) 3.76 (s, 3 H) 3.78 (s, 3 H) 4.00 (s, 3 H) 4.80 (s, 2 H) 5.13 – 5.37 (m, 2 H) 6.22 (d, J=2.2 Hz, 1 H) 6.28 (s, 1 H) 6.34 (dd, J=8.4, 2.2 Hz, 1 H) 6.81 (d, J=8.4 Hz, 1 H) 7.06 (s, 1 H) 7.32 (s, 1 H) 13.66 (br. s, 1 H). LC-MS 633.5 [M+H]+, RT 1.85 min.

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; PTC THERAPEUTICS, INC.; BRANSTROM, Arthur; JOSYULA, Vara Prasad, Venkata Nagendra; ARNOLD, Michael, Andrew; GERASYUTO, Aleksey, I.; KARP, Gary; WANG, Jiashi; WO2013/33228; (2013); A1;,
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Adding a certain compound to certain chemical reactions, such as: 23877-12-5, name is tert-Butyl 2-bromo-2-methylpropanoate, 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 23877-12-5, 23877-12-5

4-Hydroxybenzaldehyde (1) (5 g, 40.9 mmol) commercially available from Sigma-Aldrich was dissolved in N, N-dimethylformamide (50 mL) and potassium carbonate ), Magnesium sulfate (1.0 eq) and Tert-Butyl-a-bromoisobutyrate (5.0 eq) (R = -CH 3) were added in this order, and the mixture was stirred at 100 C for 22 hours. The reaction mixture was diluted with water and then extracted with ethyl acetate. The organic solvent layer was dried by adding anhydrous sodium sulfate, filtered, distilled, and purified by flash column chromatography to obtain the compound 2a (R = -CH3).

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, tert-Butyl 2-bromo-2-methylpropanoate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Seoul National University R&DB Foundation; PARK, SEUNG-BUM; KOH, MIN-SEOB; KOO, JA-YOUNG; (32 pag.)KR101727634; (2017); B1;,
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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. 252881-74-6 name is tert-Butyl 3-(2-(2-(2-aminoethoxy)ethoxy)ethoxy)propanoate, 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. 252881-74-6

To a solution of tert-butyl 13-amino-4,7,10-trioxadodecanoate (0.80 g, 2.89 mmol) in 30 mL of dioxane with stirring was added 10 mL of HCl (36%).After 0.5 hours,TLC analysis showed the reaction was complete, and the reaction mixture was concentrated,And co-concentrated with ethanol and ethanol / toluene,The title product was obtained as the hydrochloride salt (> 90% purity, 0.640 g, 86% yield) without further purification.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, tert-Butyl 3-(2-(2-(2-aminoethoxy)ethoxy)ethoxy)propanoate, and friends who are interested can also refer to it.

Reference:
Patent; Hangzhou Duo Xi Biological Technology Co., Ltd.; Zhao Luoboyongxin; Huang Yuanyuan; Yang Qingliang; Gai Shun; Ye Hangbo; Xu Yifang; Guo Huihui; Cao Minjun; Li Wenjun; Cai Xiang; Zhou Xiaomai; Xie Hongsheng; Jia Junxiang; Guo Zhixiang; Lin Chen; Yang Yanlei; Ye Zhicang; Qi Tafamingrenqingqiubugongkaixingming; (338 pag.)CN110621673; (2019); A;,
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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. 443-26-5, name is Ethyl 2-fluorobenzoate, A new synthetic method of this compound is introduced below., 443-26-5

A mixture of compound 20-1 (2 g, . 0535 mol), Boc piperazine 20-2 (3.32 g, . 017F mol, Aldrich), K2CO3 (7.39 g, . 0535 mol) and copper (. 0756 g, . 00119 mmol) in DMF (25 ML) was refluxed at 185 C overnight. The solution was cooled to room temperature, poured into 50 ML of ice water (50 ML) and extracted with EtOAc (3 x 50 mL). The combined organic layers were dried and concentrated in vacuo to give compound 20-3.

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; MERCK & CO. INC.; WO2004/78716; (2004); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

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. 94-60-0 name is Dimethyl cyclohexane-1,4-dicarboxylate, 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. 94-60-0

Comparative Examples 1-3Using the same procedure as in Examples 7-9, DMCD was hydrogenated using a commercially available copper chromite catalyst. Analysis of the reactor effluent was carried out by gas chromatography and the results are shown in Table 3 as area %. TABLE 3 DMCD Hydrogenation Using Copper Chromite Catalyst Press: 345 barg Feed Rate: 1500 mL/hour Catalyst: CuCr Comp. Temp Mono- trans cis % cis/trans Example ( C.) DMCD ester CHDM CHDM MeOH Water Imp. Conv Ratio 1 205 19.3 11.2 17.6 20.3 31.0 0.3 0.3 77.4 1.2 2 215 16.4 10.6 24.2 23.0 25.8 0.1 0.1 82.6 1.0 3 225 8.3 6.3 26.7 21.3 36.8 0.3 0.2 90.0 0.8

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Dimethyl cyclohexane-1,4-dicarboxylate, and friends who are interested can also refer to it.

Reference:
Patent; Eastman Chemical Company; US6919489; (2005); B1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

18595-18-1, A common compound: 18595-18-1, name is Methyl 3-amino-4-methylbenzoate, belongs to esters-buliding-blocks compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below.

The requisite 4-methyl-3-(pyridine-4-carbonylarnino)benzoic acid starting material (Step3) was prepared as follows: Step 1: Preparation of methyl 4-methyl-3-(pyridine-4-carbonylamino)benzoate; A solution of methyl 3-amino-4-methyl-benzoate (8.255 g, 50 mmol) and TEA (13.9 mL, 100 mmol, 2 eq) in DCM (200 mL) was cooled in an ice-bath and pyridine-4-carbonyl chloride (9.795 g, 55 mmol, 1.1 eq) was added portionwise as a solid. The reaction mixture was stirred for 30 mins, the ice-bath was removed, and stirring continued for a further 1 hr. Extra acid chloride (2 g, 0.2 eq) was added and the reaction mixture stirred a further 1 hr. It o was then diluted with more DCM and the resulting solution washed sequentially with water (twice), saturated sodium bicarbonate solution, and brine. At this stage a solid started to precipitate out, so more DCM was added. The solid precipitate (2 g) was isolated by titration and the filtrate dried (PS Paper) and evaporated to give a solid (10.7 g). The two fractions were identical (NMR, LCMS) and combined to give the title compound (12.7 g) 5 as a yellow solid, 1H NMR (400.132 MHz, DMSO) 62.33 (s, 3H),3.86 (s, 3H),7.46 (d, 1H),7.79 (d, 1H),7.87 -7.94 (m, 2H),7.98 – 8.05 (m, 1H),8.81 (d, 2H),10.35 (s, IH), m/z 271 (M+H+) 269 (M-H”).

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, Methyl 3-amino-4-methylbenzoate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2008/59214; (2008); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

57486-68-7, 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. 57486-68-7, name is Methyl 2-chlorophenylacetate, A new synthetic method of this compound is introduced below.

General procedure: To a solution of dry diisopropylamine (0.3 mL, 2.17 mmol) in dry THF (3 mL) in two-necked flask was added n-butyllithium (2.5M solution in hexane, 0.87 mL, 2.17 mmol) at -78 to 0 for 1 h, and recooled to -78 , the acetic ester (6a-f, 200 mg, 1.083 mmol) dissolved in dry THF (6.4 mL) was added by a syringe within 30 min. The mixture was stirred at -78 for 30 min, and subsequently the 4a-d (260 mg, 1.192 mmol) dissolved in dry THF (2.6 mL) was added by syringe. The mixture was vigorously stirred for 3 h. The reaction mixture was quenched by ammonium chloride aqueous solution and the mixture was extracted with ethyl acetate, the organic layer was dried over sodium sulfate, filtered and concentrated reduced pressure. The residue was purified by flash column chromatography (SiO2, EA/Hex=1/10) to give 7a-v.

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:
Article; Park, Jung-Eun; Song, Chiman; Choi, Keehyun; Sim, Taebo; Moon, Bongjin; Roh, Eun Joo; Bioorganic and Medicinal Chemistry Letters; vol. 23; 20; (2013); p. 5515 – 5518;,
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Ester – an overview | ScienceDirect Topics