Month: November 2020

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. 25662-28-6 name is Methyl 1-cyclopentene-1-carboxylate, 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. 25662-28-6

To a stirred solution of methyl cyclopent-1-enecarboxylate (2.0 g, 15.89 mmol) in DCM (15.0 mL) was added (benzyl((trimethylsilyl)methyl)amino) methyl methanesulfonate (4.0 mL, 15.88 mmol) at rt and the mixture stirred at 0 C. for 15 min followed by the drop wise addition of trifluoroacetic acid (0.50 mL). The mixture was then stirred for 16 h at rt. After completion of reaction (by TLC), solvent was evaporated, water added (50.0 mL) followed by extraction with EtOAc (3¡Á100 mL) and the combined organic layer washed with brine, dried over anhydrous Na2SO4, filtered and evaporated under reduced pressure. The crude residue was purified over 100-200 M silica-gel using 7% EtOAc:hexane to obtain the product as a light yellow liquid (1.50 g, 75% yield). MS: 260.16 [M+H]+.

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

Reference:
Patent; BIOTA EUROPE LTD.; US2012/88750; (2012); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Adding some certain compound to certain chemical reactions, such as: 14062-24-9, name is Ethyl 4-chlorophenylacetate, 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 14062-24-9. 14062-24-9

General procedure: Sodium hydride (60% in oil, 6.0g, 0.15mol) was added portionwise over a period of 15min to an ice-cold mixture of arylacetate (0.03mol) and ethyl formate (22.2g, 0.30mol) in dry Et2O (150mL). Once addition was complete, cooling bath was removed and the reaction mixture was left at room temperature for 12h and then carefully poured into cold water (200mL). The biphasic mixture was acidified with small portions of conc. aq. HCl until steady pH 2-3 was achieved. Layers were separated, organic phase was washed with brine, dried over Na2SO4 and concentrated under reduced pressure to dryness. Hydroxyacrylates 1a30 (yield 81%) and 1b30 (90%) were purified by distillation. Compounds 1c30 (70%) and 1d31 (75%) were washed by decantation with several small portions of cold petroleum ether. Characterization data are given in ESI.

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 Ethyl 4-chlorophenylacetate.

Reference:
Article; Shestakov, Aleksandr N.; Pankova, Alena S.; Golubev, Pavel; Khlebnikov, Alexander F.; Kuznetsov, Mikhail A.; Tetrahedron; vol. 73; 27-28; (2017); p. 3939 – 3948;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

207346-42-7, A common heterocyclic compound, 207346-42-7, name is Methyl 2-amino-4,5-difluorobenzoate, molecular formula is C8H7F2NO2, 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.

Example 30; 2-(5-chlorothiophen-2-yl)-2-(‘4-(6-fluoro-7-(methylaminoV2,4-dioxo-l,2-dihvdroquinazolin- 3(4H)-ylN)-3-methoxybenzamido)acetic acid (51); Scheme 7; [0151] To difluoroanthranalide Ic (5.69 g, 30 mmol), was added phosgene in toluene ((1.9 M, 160 mL, 300 mmol). The reaction mixture was stirred at rt overnight, concentrated in vacuo, evaporated from toluene (20 mL), and dried under vacuum to afford a light beige solid 8a. The material was found to give the desired urea when treated with ammonia but was not otherwise characterized.

The synthetic route of 207346-42-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PORTOLA PHARMACEUTICALS, INC.; WO2008/36843; (2008); A2;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

18013-97-3, 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. 18013-97-3, name is Diethyl 2,5-dibromoterephthalate, This compound has unique chemical properties. The synthetic route is as follows.

Compound A under nitrogen stream in 500 ml flask add (4,8-bis(5-(2-ethylhexyl)thiophen-2-yl)benzo[1,2-b: 4,5-b’]dithiophene, 15 g, 0.0259 mol) and add tetrahydrofuran(THF) was dissolved in 100 ml and slowly added 10.6 ml of n-BuLi (2.5M in hexane) at 0C ,It stirred at 50C for 1 hour 30 minutes. After stirring, the solution was cooled to -78C., and the dried ZnCl 2 solution was slowly added to the reaction solution and diethyl 2,5-bromotetraphthalate(diethyl 2,5-dibromoterephthalate, 3.93 g, 0.010364 mol) was added thereto, and the mixture was refluxed and stirred for 12 hours. After completion of the reaction and extracted with water and dichloromethane (MC),Dry the organic layer with MgSO4 and perform column chromatography(hexane: MC = 2: 1)Compound B (11.9 g, 84%) was obtained.

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; Gyeongsang National University Industry-Academic Cooperation Foundation; Kwon Sun-gi; Kim Yun-hui; Kim Myeong-jong; (22 pag.)KR2019/64410; (2019); A;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

A common compound: 24398-88-7, name is Ethyl 3-bromobenzoate, 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. 24398-88-7

The zinc reagent 2c was prepared according to TP1 from methyl3-bromo-4-(((trifluoromethyl)sulfonyl)oxy)benzoate (1c,7.26 g, 20 mmol), Zn-powder (3.92 g, 60 mmol) and InCl3(0.33 g, 1.5 mmol). The reaction mixture was stirred in DMPU(20 mL) at 50 C for 2 h. Iodolysis indicated a yield of 70% bimetallic reagent (14 mmol). The solution containing the zinc reagent was separated from the remaining zinc powder and transferred to a new flask containing a solution of ethyl 3-bromobenzoate (3e, 9.16 g, 40 mmol) and PEPPSI-iPr (0.19 g,0.28 mmol) in THF (20 mL). The reaction mixture was stirred at 50 C for 12 h before being quenched with HCl (2 M, 50 mL). Flash column chromatographical purification on silica gel(pentane/diethyl ether = 4:1) afforded 4e as a colorless oil (3.82 g, 8.83 mmol, 63%).

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, 24398-88-7, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Klatt, Thomas; Bluemke, Tobias D.; Ganiek, Maximilian A.; Knochel, Paul; Synthesis; vol. 46; 3; (2014); p. 290 – 294;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

140-39-6, Adding some certain compound to certain chemical reactions, such as: 140-39-6, name is p-Tolyl Acetate, 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 140-39-6.

General procedure: Powdered anhydrous AlCl3 (186 g, 1.4 mol) was added little by little to acetic acid phenyl ester b1 (95.3 g, 0.7 mol) in a round-bottomed flask in an ice-water bath. The resultant mixture was heated to 120 C for 6 h in an oil bath. Then the reaction mixture was added a lot of crushed ice for hydrolysis. The new formed organic layer in the reaction mixture was extracted by EtOAc, dried over anhydrous Na2SO4, and filtered off by suction filtration. The solvent was removed under reduced pressure to give the crude product, which was then purified by chromatography on silica using petroleum ether/ethyl acetate as the eluent. o-hydroxyacetophenone c1 (20.1 g, 21%) was obtained

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 140-39-6.

Reference:
Article; Tu, Qi-Dong; Li, Ding; Sun, Yao; Han, Xin-Ya; Yi, Fan; Sha, Yibamu; Ren, Yan-Liang; Ding, Ming-Wu; Feng, Ling-Ling; Wan, Jian; Bioorganic and Medicinal Chemistry; vol. 21; 11; (2013); p. 2826 – 2831;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 28868-76-0, name is Dimethyl 2-chloromalonate, 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 28868-76-0, 28868-76-0

a) Dimethyl (o-methylthio)phenoxymalonate was obtained from dimethyl chloromalonate and (o-methylthio)phenol in analogy to Example 1, paragraph c). From 17 g of (o-methylthio)phenol there were obtained 23 g of malonate from toluene-hexane.

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, Dimethyl 2-chloromalonate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Hoffmann-La Roche Inc.; US5292740; (1994); A;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

A common heterocyclic compound, 33993-24-7, name is Cyclopropanecarboxylic anhydride, molecular formula is C8H10O3, 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. 33993-24-7.

General procedure: To a stirred solution of 7 (107 mg, 0.20 mmol), TEA (82 muL,0.60 mmol) and DMAP (10 mg, 0.08 mmol) in dry DCM (10mL) acetic anhydride (57 muL, 0.60 mmol) was added dropwiseat 0 C. Then, the reaction mixture was allowed to stir at roomtemperature overnight. The mixture was concentrated anddiluted with H2O (20 mL) and extracted with EtOAc (2¡Á10mL). The combined organic layers were washed with H2O(2¡Á20 mL), brine (20 mL), and dried over Na2SO4. The mixturewas cooled to room temperature, slowly diluted with H2O(100 mL) and extracted with EtOAc (2¡Á100 mL). The combinedorganic layers were washed with H2O (2¡Á150 mL), brine(150 mL), dried over Na2SO4 and concentrated. The residuewas purified by flash chromatography using 5% EtOAc inpetroleum ether to yield 77 mg (0.13 mmol, 65%) of product asa white pure solid.

The synthetic route of Cyclopropanecarboxylic anhydride has been constantly updated, and we look forward to future research findings.

Reference:
Article; Wang, Xiao-Yin; Zhang, Shu-Yong; Li, Jing; Liu, Hua-Nan; Xie, Xin; Nan, Fa-Jun; Acta Pharmacologica Sinica; vol. 35; 11; (2014); p. 1463 – 1472;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

4606-07-9, A common compound: 4606-07-9, name is Ethyl cyclopropanecarboxylate, 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.

Example 126a 3-Cyclopropyl-3-oxopropanenitrile 126a To a solution of acetonitrile (0.34 mL, 6.58 mmol) in THF (3 mL) at -78 C. under N2 protection was added lithium di-i-propylamide (3.3 mL, 2M in THF, 6.58 mmol) drop-wise. The reaction mixture was stirred at -78 C. for 3 h. Then ethyl cyclopropanecarboxylate (0.50 g, 4.38 mmol) in THF (2 mL) was added and the mixture was allowed to warm to room temperature for a period of 1 h. Water (2 mL) was added and the solvent was removed under reduced pressure. Dichloromethane (2 mL) was added and the pH of the mixture was adjusted to 5 with 2N HCl. It was then extracted with dichloromethane (5 mL*2). The combined organic layer was dried over Na2SO4 and concentrated to afford 126a as a yellow oil, which was used in the next step without further purification.

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 cyclopropanecarboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; GENENTECH, INC.; Crawford, James John; Ortwine, Daniel Fred; Wei, BinQing; Young, Wendy B.; US2013/116246; (2013); 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. 14062-25-0, name is Ethyl 2-(4-bromophenyl)acetate, This compound has unique chemical properties. The synthetic route is as follows., 14062-25-0

Synthesis of compound 166.1. To a solution of ethyl 161.1 (5.0g, 20.6 mmol, l .Oeq) in CH2CI2 (50 mL) was added preraformaldehyde (0.938g, 24.69mmol, 1.2eq) followed by tetrabutylammonium chloride (0.571g, 2.05mmol, O. leq), and K2CO3 (6.2g, 45.26mmol, 2.2eq). The reaction was stirred at 60 C 3h. The reaction mixture was quenched with ice cold water and product was extracted with CH2CI2 (50mL x 2). Organic layer were combined and dried over sodium sulphate and concentrated under reduced pressure to obtain 166.1 (2.5g, 47.65%). MS (ES):256.4 m/z [M+H]+.

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; NIMBUS LAKSHMI, INC.; MASSE, Craig E.; GREENWOOD, Jeremy Robert; ROMERO, Donna L.; HARRIMAN, Geraldine C.; WESTER, Ronald T.; SHELLEY, Mee; KENNEDY-SMITH, Joshua Jahmil; DAHLGREN, Markus; WO2015/131080; (2015); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics