Tag: M.W=100-200

33993-24-7, The chemical industry reduces the impact on the environment during synthesis 33993-24-7, name is Cyclopropanecarboxylic anhydride, I believe this compound will play a more active role in future production and life.

To a suspension of Compound Int-28d (0.51 g, 1.87 mmol) in CH2C12 (3 mL) was added cyclopropyl anhydride (2 mL). The resulting reaction was allowed to stir at room temperature for 2 hours, then a solution of 4M HC1 in dioxane ( 3 mL) was added and the reaction was allowed to stir at room temperature for 2 hours. The reaction mixture was then filtered and the collected solid was washed with hexane and dried under vacuum to provide Compound Int-29a (590 mg). MS (ESI) m / e (M+H+): 323.

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

Reference:
Patent; MERCK SHARP & DOHME CORP.; KOZLOWSKI, Joseph, A; ROSENBLUM, Stuart, B; COBURN, Craig, A; SHANKAR, Bandarpalle, B; ANILKUMAR, G, Nair; CHEN, Lei; DWYER, Michael, P; JIANG, Yueheng; KEERTIKAR, Kartik, M; LAVEY, Brian, J; SELYUTIN, Oleg, B; TONG, Ling; WONG, Michael; YANG, De-Yi; YU, Wensheng; ZHOU, Guowei; WU, Hao; HU, Bin; ZHONG, Bin; SUN, Fei; JI, Tao; SHEN, Changmao; WO2012/40923; (2012); 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. 37746-78-4, name is (E)-Ethyl 4-bromobut-2-enoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. 37746-78-4

The compound of formula 7-4 (3.0 g, 8.7 mmol, 1 eq) was dissolved in acetonitrile,Ethyl bromocrotonate (1.86 g, 9.6 mmol, 1.1 eq) and potassium carbonate (2.42 g, 17.5 mmol, 2 eq) were added. After the addition, the temperature was raised to 85 C. and the reaction was continued overnight.After the completion of the reaction by thin layer chromatography, the mixture was filtered and spin-dried. Ethyl acetate and water were dissolved and diluted. The layers were separated, and the aqueous phase was extracted with ethyl acetate. The organic phase was combined.After washing with saturated saline, it was dried over anhydrous sodium sulfate, filtered, and spin-dried to obtain 3.94 g of a brown oil (compound of formula 7-5) in 98% yield.

The synthetic route of 37746-78-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Shanghai Yangfan Pharmaceutical Technology Co., Ltd.; Chen Youxi; Gao Fei; He Lidong; (80 pag.)CN104109143; (2018); B;,
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Some common heterocyclic compound, 1865-29-8, name is Methyl 2-phenylacrylate, molecular formula is C10H10O2, 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. 1865-29-8

PREPARATION 21 Methyl (RS)-4-cyano-2-Phenylbutanoate STR75 Lithium diisopropylamide (3.67 ml of a 1.5 molar solution in cyclohexane) was added to acetonitrile (0.26 ml) in tetrahydrofuran (10 ml) at -78 C. After 1 hour, methyl 2-phenyl-acrylate (see Preparation 22) (0.81 g) in tetrahydrofurn (10 ml) was added and the mixture was stirred for 1 hour, allowed to warm to room temperature then treated with saturated ammonium chloride solution. The resulting mixture was partitioned between ethyl acetate and water, the organic phase dried over magnesium sulphate and evaporated to give a residue which was partitioned between ether and 10% aqueous sodium carbonate. The organic layer was dried over magnesium sulphate and evaporated to leave the title compound (0.5 g, 75%) as an oil. 1 H-NMR (300 MHz, CDCl3), delta=2.0-2.4 (m, 4H), 3.7 (s, 3H), 3.8 (t, 1H), 7.2-7.5 (m, 5H) ppm. I.R. (thin film) 2220 cm-1 (C=N).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1865-29-8, its application will become more common.

Reference:
Patent; Pfizer Inc.; US5292749; (1994); A;,
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25597-16-4, A common compound: 25597-16-4, name is Ethyl 4,4,4-trifluorocrotonate, 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.

Step 6: ethyl 8-chloro-6-(methyl-D3)-2-(trifluoromethyl)-2H-chromene-3-carboxylate The resulting product (0.25 g, 1.4 mmol) from step 5, ethyl 4,4,4-trifluorocrotonate (0.48 g, 2.8 mmol) and anhydrous potassium carbonate (0.46 g, 2.8 mmol) were dissolved in DMF (10 mL), and then the system was stirred for 3 hrs at 90 C. At the end of reaction, the reaction system was cooled to room temperature and added with water, the mixture was extracted with ethyl acetate, and the organic phase was dried and evaporated in vacuum to obtain 0.2 g of the product (44%) by column chromatography. 1HNMR (400 MHz, d6-DMSO), delta 7.39 (s, 1H), 7.31 (s, 1H), 6.1 (m, 1H), 4.27 (dd, 2H), 1.30 (t, 3H) MS (MM-ES+APCI), m/z: 325 (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, Ethyl 4,4,4-trifluorocrotonate, other downstream synthetic routes, hurry up and to see.

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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25597-16-4, 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.

The resulting product (0.45g, 1.9mmol) from step 4, ethyl 4,4,4-trifluorocrotonate (1.3g, 7.6mmol) and anhydrous potassium carbonate (2.6g, 1.9mmol) were dissolved in DMF (10mL), and then the system was stirred for 2hrs at 90C. At the end of reaction, the reaction system was cooled to room temperature and added with water, the mixture was extracted with ethyl acetate, and the organic phase was dried and evaporated in vacuum to obtain 0.40g of the product (55%) by column chromatography. 1HNMR (400 MHz, d-CDCl3), delta 7.88(s, 1H), 6.76 (s, 1H), 5.7(m, 1H), 4.3(dd, 2H),1.35(t, 3H) MS (MM-ES+APCI), m/z: 384 (M-H+)

The synthetic route of 25597-16-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Guangzhou Institute 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; EP2845854; (2015); A1;,
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3196-15-4, Name is Methyl 2-bromobutyrate, 3196-15-4, 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.

Example 1. Synthesis of benzo bis-furan compound IV-1 (1) In a round-bottom flask equiped with a reflux condenser and a magnetic stirrer, 0.5135g (1.0mmol) of compound I dissolved in 10mL DMF and 0.346g (2.5mmol) potassium carbonate was added. The reaction was stirred at room temperature. After ten minutes, 0.272g (1.5mmol) 2-bromobutyric acid methyl ester VI-a-1 was added and stirring was continued for 5h. After completion of the reaction, 30mL of dichloromethane was added with copious amount of water (80mL¡Á5) until removal of DMF. The organic phase was seperated, dried over anhydrous magnesium sulfate, concentrated, and purified by TLC (E/P [ethyl acetate:petroleum ether] = 1:5) to give the benzofuran II-a-1. Yield 75%

Statistics shows that Methyl 2-bromobutyrate is playing an increasingly important role. we look forward to future research findings about 3196-15-4.

Reference:
Patent; Zhejiang University; Wang, Yuguang; Zhu, Bingchun; Liu, Juanfang; Li, Qingsi; (14 pag.)CN104016998; (2016); B;,
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Some common heterocyclic compound, 4341-76-8, name is Ethyl 2-butynoate, molecular formula is C6H8O2, 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. 4341-76-8

General procedure: In a two neck rbf was stirred a mixture of Pd(OAc)2 (275 mg,1.22 mmol) and TDMPP (540 mg, 1.22 mmol) in benzene (30 ml)for 15 min at rt under nitrogen. To this mixture was added ethyl-2-butynoate 7 (2.84 ml, 24.48 mmol) and the resulting mixturewas further stirred for 10 min at rt. Next, ethynylbenzene 4a(2.50 g, 24.48 mmol) was added to this solution and the mixturewas stirred for 5-10 min until reaction was completed. Theworkup of reaction was performed by evaporating the solvent invacuum followed by column chromatography (Hexane:EtOAc = 100:1) to give the desired compound 8a (2.62 g);

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4341-76-8, its application will become more common.

Reference:
Article; Singh, Sarbjit; Goo, Ja-Il; Noh, Hyojin; Lee, Sung Jae; Kim, Myoung Woo; Park, Hyejun; Jalani, Hitesh B.; Lee, Kyeong; Kim, Chunsook; Kim, Won-Ki; Ju, Chung; Choi, Yongseok; Bioorganic and Medicinal Chemistry; vol. 25; 4; (2017); p. 1394 – 1405;,
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A common heterocyclic compound, 35180-01-9, name is Chloromethyl isopropyl carbonate, molecular formula is C5H9ClO3, 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. 35180-01-9.

S03 condensation: After pretreating the crude tenofovir obtained in the step S02, and stirring 16 L of N-methylpyrrolidone and 4.44 kg of triethylamine, the temperature is raised to 50 C and stirred.11.15 kg of isopropyl chloromethyl carbonate was added dropwise, stirred, and the reaction was completely cooled and quenched.After cooling, add 12 L of cyclohexane twice, stir, centrifuge, layer, and discard the upper layer of cyclohexane. The lower layer of the filtrate was transferred to a reaction kettle, and 30 L of water and 20 L of ethyl acetate were added.After stirring for 30 minutes, the layers were allowed to stand, and the aqueous layer was extracted with 10 L of ethyl acetate.Wash with 20L of 10wt% brine, add 1.0kg anhydrous sodium sulfate, stir dry, centrifuge,The filtrate is transferred to the transfer reactor in batches, concentrated under reduced pressure, and the concentrate is transferred to the reaction vessel.Denotefovir dipivoxilCrude.

The synthetic route of Chloromethyl isopropyl carbonate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Shandong Kexing Biological Products Co., Ltd.; Hao Zhihai; Wang Cuicui; Lu Fuxin; Guo Chao; Wang Jun; Zhang Yun; Qiu Duxian; Cui Ning; (26 pag.)CN108409789; (2018); A;,
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2555-28-4,Some common heterocyclic compound, 2555-28-4, name is 7-Methoxy-4-methylcoumarin, molecular formula is C11H10O3, 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.

(0.95 g, 5 mmol) of 4a, 50 mL of xylene was added to a round bottom flask,Stir and heat, so that it gradually dissolved.Then, selenium dioxide (0.55 g, 5 mmol) was added and the reaction was refluxed for 12 h.Stop heating, hot suction filter, the filtrate cold with yellow solid precipitation, The filtrate was concentrated under reduced pressure to give a yellow solid 4b (0.85 g, yield 84%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2555-28-4, its application will become more common.

Reference:
Patent; Shandong He Bentang Biological Technology Co., Ltd.; Pan Xuan; Zhang Chengrui; Wang Huili; (9 pag.)CN106317029; (2017); A;,
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10601-80-6, 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. 10601-80-6, name is Ethyl 3,3-diethoxypropionate, This compound has unique chemical properties. The synthetic route is as follows.

Example 25 Preparation of 3,3-diethoxypropanoic acid Ref. . To a 250 mL round-bottomed flask with magnetic stirring that contained ethyl 3,3-diethoxypropanoate (20.0 g, 102.0 mmol, colourless oil, 97 %), a previously prepared solution of NaOH (5.23 g, 131.0 mmol) in H2O (30 mL) was added. The resulting mixture was stirred to reflux (100 C) during 1h. After allowing it to temper, the mixture was acidified using HCl 37 % and it was extracted with AcOEt, 8x 20 mL. The resulting organic phase was washed with 1x 20 mL NaCl sat., dried with Na2SO4, filtered and concentrated to dryness. The obtained oil was confirmed to correspond to the title compound (15.9 g, 98.0 mmol, 96 %).

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; Esteve Quimica, S.A.; EP2418192; (2012); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics