Esters-buliding-blocks

Adding a certain compound to certain chemical reactions, such as: 18595-12-5, name is Methyl 5-amino-2-methylbenzoate, 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 18595-12-5, Safety of Methyl 5-amino-2-methylbenzoate

General procedure: To a solution of compound 11a (154 mg, 1.0 mmol) in anhydrous CH2Cl2 (10 mL) was added 3,5-dichlorobenzoyl chloride (209 mg, 1.0 mmol) and pyridine (241 mL 3.0 mmol) under ice bath. After stirring at room temperature for about 8 h, the solvent was removed in vacuum. The resulting residue was dissolved in NaOH (1 M) water solution (3 mL) and CH3OH (3 mL) and stirred for another 2 h. Then the solvent was removed under vacuum, and the residue was acidied to pH 2 or below with HCl (1 M) water solution. The solution was extracted with ethyl acetate twice and the combined organics were dried over anhydrous sodium sulfate and concentrated in vacuum. The resulting residue was puried by silica gel chromatography to give the desired compound as a white solid (234 mg, yield 85.0%)

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:
Article; Gao, Ding-Ding; Dou, Hui-Xia; Su, Hai-Xia; Zhang, Ming-Ming; Wang, Ting; Liu, Qiu-Feng; Cai, Hai-Yan; Ding, Hai-Peng; Yang, Zhuo; Zhu, Wei-Liang; Xu, Ye-Chun; Wang, He-Yao; Li, Ying-Xia; European Journal of Medicinal Chemistry; vol. 154; (2018); p. 44 – 59;,
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Some common heterocyclic compound, 65868-63-5, name is tert-Butyl 6-bromohexanoate, molecular formula is C10H19BrO2, 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. Recommanded Product: tert-Butyl 6-bromohexanoate

To a stirred mixture of alcohol 32 (49.7 mg, 0.10 mmol) and TBAI (3.7 mg,0.01 mmol) in DMF (1 mL) at rt was NaH (4.4 mg, 60% dispersion in mineraloil, 0.11 mmol). After 30 minutes, tert-butyl bromohexanoate (25.1 mg, 0.1mmol) was added and the solution was stirred for a further 16 h at rt. H2O (1mL) was then added, and the mixture was extracted with ether (3 ¡Á 2 mL), driedover MgSO4, filtered and concentrated in vacuo. The resultant crude oil was purified by flashchromatography (EtOAc-hexanes 1:3) giving the product as a pale oil (10 mg, 17%). vmax(neat)/cm-12856, 1727, 1367, 1104, 845; deltaH (400 MHz; CDCl3), 7.41 (d, J = 2.0 Hz), 7.32 (dt, J = 8.3, 1.7, 2H),7.27 (m, 2H), 7.03 (dt, J = 8.5, 2.0, 2H), 3.60 (t, J = 6.8, 2H) 3.47 (q, J = 6.4, 2H), 2.87 (t, J = 4.8, 4H),2.66 (t, J = 7.1, 2H), 2.37 (s, 3H), 2.20 (m, 4H), 1.75 (m, 4H), 1.60 (m, 6H), 1.44 (s, 9H); HRMS (ESI+)[M + H]+ 667.2817 calcd for C36H45Cl2N4O4 667.2812.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 65868-63-5, its application will become more common.

Reference:
Article; Grant, Phillip S.; Kahlcke, Nils; Govindpani, Karan; Hunter, Morag; MacDonald, Christa; Brimble, Margaret A.; Glass, Michelle; Furkert, Daniel P.; Bioorganic and Medicinal Chemistry Letters; vol. 29; 21; (2019);,
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Some common heterocyclic compound, 939-18-4, name is 3-Bromo-2H-chromen-2-one, molecular formula is C9H5BrO2, 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. name: 3-Bromo-2H-chromen-2-one

Step 2: 3-({3-[4-(isoquinolin-1 -yl)piperazin-1 -yl]propyl}amino)-2H-chromen- 2-one hydrochloride (87) A mixture of intermediates 31 b (50 mg, 0.185 mmoles, 1 eq.) and 87a (50 mg, 0.222 mmoles, 1 .2 eq.), Pd(OAc)2 (5 mg, 0.019 mmoles, 0.1 eq.), Xantphos (1 1 mg, 0.019 mmoles, 0.1 eq.) and Cs2C03 (90 mg, 0.28 mmoles, 1 .5 eq.) in 1 ,4-dioxane (2.5 ml_) was heated to 130C in a sealed tube under microwave irradiation for 2 hours. The reaction mixture was concentrated under reduced pressure and the residue was chromatographed on silica gel (SNAP25) eluting with a gradient of 0-2% mixture A in dichloromethane, where mixture A is MeOH/NH4OH 10:1 . The partially pure product was further purified by preparative LC-MS to give 20 mg of a yellow gum. The product was dissolved in dichloromethane (4 mL) and treated with 1 M HCI solution in diethyl ether (0.16 mL) causing precipitation. The resulting mixture was evaporated under reduced pressure and the residue was triturated with diethyl ether. The solids were dried to give 24 mg of 3-({3-[4-(isoquinolin-1 – yl)piperazin-1 -yl]propyl}amino)-2H-chromen-2-one hydrochloride 87 (Y=27%). LC-MS (M-H+) = 415.3. 1 H NMR (400MHz, DMSO-d6) delta = 1 1 .1 6 (br. s., 1 H), 8.19 (d, J=7.5 Hz, 1 H), 8.08 (d, J=5.8 Hz, 1 H), 8.00 (d, J=7.5 Hz, 1 H), 7.85 (t, J=6.5 Hz, 1 H), 7.70 (t, J=7.3 Hz, 1 H), 7.57 (d, J=5.3 Hz, 1 H), 7.47 (br. s., 1 H), 7.37 – 7.10 (m, 3H), 6.68 (s, 1 H), 6.27 (br. s., 1 H), 4.00 (d, J=12.3 Hz, 2H), 4.37 – 3.81 (m, 1 H), 3.64 (d, J=1 1 .0 Hz, 4H), 3.40 (d, J=9.3 Hz, 2H), 3.28 (d, J=5.8 Hz, 4H), 2.1 1 (br. quin, J=7.0 Hz, 2H)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 939-18-4, its application will become more common.

Reference:
Patent; AZIENDE CHIMICHE RIUNITE ANGELINI FRANCESCO A.C.R.A.F. S.P.A.; OMBRATO, Rosella; GAROFALO, Barbara; MANGANO, Giorgina; CAPEZZONE DE JOANNON, Alessandra; CORSO, Gaia; MAGARO’, Gabriele; FURLOTTI, Guido; IACOANGELI, Tommaso; (108 pag.)WO2016/96631; (2016); A1;,
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Synthetic Route of 25597-16-4, The chemical industry reduces the impact on the environment during synthesis 25597-16-4, name is Ethyl 4,4,4-trifluorocrotonate, I believe this compound will play a more active role in future production and life.

EXAMPLE 14 STR89 Step A: Preparation of 4,4,4-Trifluorocrotonic acid A solution of ethyl 4,4,4-trifluorocrotonate (9.85g, 65.9 mmole) and 1N NaOH (92.3 mL, 92.3 mmole) in THF (24 mL) was stirred at room temperature for 3 hours. The pH was brought to 1 with conc. HCl and the mixture extracted with Et2 O (3*). The combined extracts were dried (MgSO4) and concentrated in vacuo to afford the title compound as an oil. NMR (CDCl3): delta 6.55 (d, 1H); 6.89 (dq, 1H).

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; Merck & Co., Inc.; US6048869; (2000); A;,
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Adding a certain compound to certain chemical reactions, such as: 69812-51-7, name is Methyl 4-chlorosulfonylbenzoate, 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 69812-51-7, Safety of Methyl 4-chlorosulfonylbenzoate

Under Ar protection,Compound 26b (0.7 g, 2.98 mmol), 100 mL of dichloromethane,Morpholine (0.31mL, 3.58mmol),Et3N (1.24 mL, 8.94 mmol) was placed in a 250 mL round-bottomed flask and reacted overnight at room temperature. The reaction was detected by TLC the next day.The organic phase was sequentially washed with a 1 mol / L hydrochloric acid aqueous solution and a saturated saline solution.Dry over anhydrous Na2SO4. Concentrated under reduced pressure to obtain Intermediate 27b, 0.78 g of a white solid, with a yield of 91.2%.

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

Reference:
Patent; Chinese Academy Of Medical Sciences Pharmaceutical Institute; Huang Haihong; Li Gang; Wang Pengxu; (55 pag.)CN110759889; (2020); A;,
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Application of 17100-65-1, 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. 17100-65-1 name is Methyl 2-bromo-4-methoxybenzoate, 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.

A stirred solution of 2-Bromo-4-methoxy-benzoic acid methyl ester (6) (2.5 g, 10.201 mmol) in DMF (15 mL) was degassed for 15 minutes with argon followed by the addition of Zn(CN)2 (2.39 g, 20.402 mmol) and Pd(PPh3)4 (1.17 g, 1.02 mmol) and the reaction mixture was stirred at 100C for 16 hours. The reaction mixture was diluted with Ethyl acetate, washed with water and brine, dried over sodium sulfate and concentrated. The crude was purified by column chromatography (silica, gradient: 20-30%) EtOAc in Hexane) to afford the Intermediate 7 (900 mg, 46%) as white solid.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Methyl 2-bromo-4-methoxybenzoate, and friends who are interested can also refer to it.

Reference:
Patent; THE BROAD INSTITUTE, INC.; THE GENERAL HOSPITAL CORPORATION; INSTITUTO CARLOS SLIM DE LA SALUD; BURNS, Sean, M.; WAGNER, Bridget, K.; VETERE, Amedeo; (189 pag.)WO2018/175324; (2018); A1;,
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Related Products of 25662-28-6, 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. 25662-28-6, name is Methyl 1-cyclopentene-1-carboxylate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

General procedure: Under nitrogen atmosphere, a mixture of in H2O (0.90muL, 0.050mmol) in THF (1mL) was added to an oven-dried reaction tube charged with (R)-H8-BINOL (22.1mg, 0.075mmol). After stirred at RT for 5min, Bu2Mg (1.0M in heptane, 50.0muL, 0.050mmol) and diarylphosphine oxide (3, 0.50mmol, 0.5M in anhydrous THF) were sequentially added and stirred for another 5min before being cooled to-20C. alpha,beta-Unsaturated ester (2, 0.50mmol) was then added, and the reaction was stirred at-20C for 2-3 days. The reaction mixture was quenched with sat. NH4Cl (2mL), diluted with H2O (5mL) and extracted with CH2Cl2 (10mL¡Á2). The combined organic phase was dried over anhydrous Na2SO4. After filtration and concentration, and the residue was purified by silica gel column chromatography (hexane: THF=5:1 to 1:1) to give the corresponding product. The enantiomeric excess was determined by the chiral HPLC analysis.

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

Reference:
Article; Cao, Meng-Yue; Xu, Zhi-Min; Gao, Wei; Liu, Juan; Tan, Fen; Lu, Hai-Hua; Tetrahedron; vol. 75; 24; (2019); p. 3282 – 3291;,
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Reference of 344-14-9, 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. 344-14-9, name is Dimethyl 2-fluoromalonate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Reference Example 1Mixture of dimethyl fluoro[(1R,5R)-5-hydroxycyclopent-2-en-1-yl]propanedioate (8a) and dimethyl fluoro[(1S,5S)-5-hydroxycyclopent-2-en-1-yl]propanedioate (8b) 23.81 g (110.2 mmol) of a 25 w/w % methanol solution of sodium methoxide (NaOMe) was added to a methanol (90.4 mL) solution of 18.19 g (121.2 mmol) of dimethyl fluoropropanedioate (7) over 3 minutes while keeping the internal temperature between 25 C. and 38 C. After stirring the solution thus obtained for 15 minutes, 4.52 g (55.1 mmol) of 6-oxabicyclo [3.1.0] hex-2-ene (6) was added thereto over 2 minutes while keeping the internal temperature between 25 C. and 38 C. After stirring at room temperature for 1 hour, 45 mL of a saturated ammonium chloride aqueous solution was added over 10 minutes while keeping the internal temperature between 26 C. and 35 C. The reaction mixture was concentrated under reduced pressure, most of the methanol was removed by evaporation, and 108 g of a brown solution containing solids was obtained. After extraction with 136 mL of ethyl acetate was carried out twice, washing with 45 mL of water was carried out. After the organic layer was concentrated under reduced pressure, 100 mL of toluene was added, and concentration under reduced pressure was carried out again. The concentrated residue was purified by flash silica gel column chromatography (eluent:toluene/ethyl acetate), thus giving 7.21 g of a mixture of the compound of the formula 8a and the compound of the formula 8b as a yellow oily substance.1H NMR (500 MHz, DMSO-d6): delta (ppm) 2.13-2.17 (m, 1H), 2.56 (dddd, J=2.2, 4.3, 7.1, 17.2 Hz, 1H), 3.32-3.40 (m, 1H), 3.77 (s, 3H), 3.79 (s, 3H), 4.20 (m, 1H), 5.04 (d, J=6.1 Hz, 1H), 5.47 (ddd, J=2.1, 4.3, 6.1 Hz, 1H), 5.85 (ddd, J=2.2, 4.4, 6.1 Hz, 1H). 13C NMR (125 MHz, DMSO-d6): delta (ppm) 41.93, 53.39 (d, J=19.5 Hz), 58.70 (d, J=20.8 Hz), 70.43 (d, J=2.6 Hz), 93.55, 95.14, 125.59, 133.32, 165.42 (d, J=15.6 Hz), 165.62 (d, J=14.3 Hz). 19F NMR (470 MHz, DMSO-d6): delta (ppm) -172.43, -172.36. HRMS(ES)m/z: [M+Na]+ calcd for CHH13O5FNa; 255.0645, found 255.0635. IR (neat) 3528, 3408, 2960, 1755, 1438, 1284, 1253, 1173, 1111, 1068, 1031, 936, 838, 787, 722, 668, 415 cm-1.

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

Reference:
Patent; TAISHO PHARMACEUTICAL CO., LTD; US2012/232304; (2012); A1;,
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Ester – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 10601-80-6, name is Ethyl 3,3-diethoxypropionate, 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 10601-80-6, Application In Synthesis of Ethyl 3,3-diethoxypropionate

General procedure: A mixture of Yb(OTf)3 (2.5 mol%), amine (1.0 eq.), ethyl 3,3-diethoxypropionate (2.5 eq.) and aldehyde (1.1 eq.) in 1,4-dioxane (1.5 mL / 1 eq.) was stirred at 90 C for 6-17 h. After the reaction, the resulting mixture was washed with PBS buffer solution (25 mL) and extracted with CH2Cl2 (15 mL¡Á3). The organic layer was dried over MgSO4. Removal of the solvent in vacuo, followed by chromatography on silica gel column (AcOEt/Hexane or CHCl3/MeOH), afforded dihydropyridine 4.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Ethyl 3,3-diethoxypropionate, and friends who are interested can also refer to it.

Reference:
Article; Sueki, Shunsuke; Takei, Ryo; Abe, Junya; Shimizu, Isao; Tetrahedron Letters; vol. 52; 34; (2011); p. 4473 – 4477;,
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Reference of 5335-05-7, 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. 5335-05-7 name is Chloromethyl benzoate, 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.

Into 2 ml of N,N-dimethylformamide was suspended 0.05 g of sodium hydride (60% oily), and 0.2 g of 3-(4-trifluoromethylpyridin-2-yl)-l,2,4-oxadiazol-5-one was added at room temperature. After stirring for 10 minutes, 0.18 g of chloromethylbenzoate, and the mixture was stirred at 70C for 3 hours. The reaction solution was allowed to cool to room temperature, and poured into an aqueous saturated ammonium chloride solution, followed by extraction with ethyl acetate three times. The organic layers were combined, washed with an aqueous saturated sodium chloride solution, dried with anhydrous magnesium sulfate, and concentrated. The residue was subjected to silica gel column chromatography to obtain 0.12 g of [3-(4- trifluoromethylpyridin-2-yl)- 1 ,2,4-oxadiazol-5-on-4-yl]methyl=benzoate (present compound (27)).Present Compound (27)1H-NMR: 6.44 (s, 2H), 7.38-7.42 (m, 2H), 7.53-7.59 (m, IH), 7.71 (d, IH), 7.79-7.92 (m, 2H), 8.30 (s, IH), 8.87 (d, IH)

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

Reference:
Patent; SUMITOMO CHEMICAL COMPANY, LIMITED; WO2009/66786; (2009); A1;,
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Ester – an overview | ScienceDirect Topics