Author: Jessica.F

541-16-2, Adding some certain compound to certain chemical reactions, such as: 541-16-2, name is Di-tert-Butyl malonate, 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 541-16-2.

General procedure: alpha,beta-Unsaturated aldehyde (3.0 mmol) and malonate (3.0 mmol) were added into asolution of TiCl4 (6.0 mmol) in CCl4 (2.0 mL) and THF (10 mL) at 0 C, Then, pyridine (0.96 mL, 12.0 mmol) in THF (2 mL) was added dropwisely over 1 h. The resulting mixture was stirred at room temperature overnight. After quenched with water, the mixture was extracted with ethyl acetate, dried over Na2SO4, filtered and concentrated under vacuum. The residue was purified by silica gel chromatography with hexane/ethyl acetate = 20/1 to afford the product.

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 541-16-2.

Reference:
Article; Wei, Xu; Lu, Junzhu; Duan, Wei-Liang; Synthesis; vol. 48; 23; (2016); p. 4155 – 4160;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 31930-34-4, name is Ethyl cis-3-Bromoacrylate, 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 31930-34-4, 31930-34-4

General procedure: Pd(PPh3)4 (0.047g, 0.042 mmol) and CuI (0.016g, mmol) were dissolved in degassed NEt3 (11 mL). (Z)- Ethyl 3-bromopropenoate1 (0.75 g, 4.2mmol) was dissolved in degassed NEt3 (1.8 mL) and slowly added to the reaction mixture. After 5 minutes, propargyl alcohol (0.23 g, 4.1 mmol) in degassed NEt3 (1.8 mL) was added dropwise and the mixture was stirred for 24 h. The contents of the flask were filtered through Celite and washed with hexanes. Saturated NH4Cl solution was added to the filtrate, which was subjected to a conventional extractive workup (CH2Cl2)(3x). The residue (0.250 g, 1.62 mmol) was dissolved in 50 mL of CH2Cl2 (50 mL) and the solution was cooled to 0 C. Excess Co2(CO)8 was added to the flask and the mixture was stirred for 30 minutes. The solution was removed from the ice bath and allowed to come to room temperature while stirring for an additional 2 h. Following solvent removal under reduced pressure, the crude product was dissolved in petroleum ether and filtered through a silica plug. The silica gel was first washed with petroleum ether to flush out excess Co2(CO)8 and then washed with diethyl ether to collect hexacarbonyl [mu-eta4((Z)- ethyl 6-hydroxyhex-2-en-4-ynoate)]dicobalt (1.103 g, 60%). IR (neat): 3465, 2984, 2902, 2051, 2002, 1704; 1H NMR : 7.03 (d, J=11.4, 1H), 5.88 (d,J=11.4, 1H), 4.87 (d, J=6.9, 2H), 4.17 (q, J=7.2, 2H), 4.11 (t, J=6.9, 1H), 1.26 (t, J=7.2, 3H); 13C NMR :198.8, 166.4, 142.8, 117.2, 98.0, 79.8, 64.5, 60.64, 14.0; MS EI m/e: 384 (M+ -2CO), 356 (M+ – 3CO), 328(M+ – 4CO), 272 (M+ – 6CO); HRMS for C14H10Co2O9, calcd (M+-2CO) 383.9090, found 383.9091.To a solution of hexacarbonyl[mu-eta4((Z)- ethyl 6-hydroxyhex-2-en-4-ynoate)]dicobalt (0.363 g,0824 mmol) was stirred in acetic anhydride (1.5 mL) and pyridine (1.5 mL), starting at 0C and warming up to room temperature. After 2 hours, the reaction was placed under reduced pressure to obtain crude product and flash chromatography was performed (10:1 petroleum ether: diethyl ether) to yield (10) as a dark red oil (0.3599 g, 91%). IR (neat) 2960, 2094, 2054, 2019, 1744, 1719; 1H NMR : 7.07 (d, J = 11.4,1H), 5.93 (d, J = 11.4, 1H), 5.478 (s, 2H), 4.18 (q, J = 7.1, 2H), 2.14 (s, 3H), 1.29 (t, J = 7.1, 3H); 13C NMR :198.8, 170.8, 165.1, 141.6, 118.5, 109.6, 93.8, 79.7, 66.2, 60.3, 20.5, 14.2; MS EI m/e: 398 (M+ – 3CO),370 (M+ – 4CO), 342 (M+ – 5CO), 314 (M+ – 6CO); HRMS for C16H12Co2O10, calcd (M+-3CO) 397.9247,found 397.9262.

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 cis-3-Bromoacrylate, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Mahmood, Aqsa; Ngenzi, Rebecca; Penner, Page M.; Green, James R.; Synlett; vol. 27; 8; (2016); p. 1245 – 1250;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

These common heterocyclic compound, 106614-28-2, name is Methyl 2,4-difluorobenzoate, 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. 106614-28-2

To a 8 mL sealed tube was added (1S,4S,5R)-5-[[l-(2-chloro-6-methylphenyl)-4- cyclopropyl-1H-pyrazol-5-yl]methoxy]-2-azabicyclo[2.2.1]heptane 8g (100 mg, 0.28 mmol, 1.00 equiv.), methyl 2,4-difluorobenzoate (72 mg, 0.42 mmol, 1.50 equiv.), CsF (0.134 g, 3.00 equiv.), and l-Ethyl-3-methylimidazolium dimethyl phosphate (1 mL). The resulting mixture was heated at 90 C overnight. After cooling to room temperature, the mixture was diluted with 20 mL of H2O, and extracted with ethyl acetate (100 mL x 2). The combined organic extracts were washed with brine (100 mL x 2), dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was purified by silica gel column chromatography eluting with ethyl acetate/petroleum ether (1 :2) to afford methyl 4-[(1S,4S,5R)-5-[[l-(2-chloro-6-methylphenyl)-4- cyclopropyl-1H-pyrazol-5-yl]methoxy]-2-azabicyclo[2.2.1]heptan-2-yl]-2-fluorobenzoate 8h (91 mg, 64%) as a red oil.

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 106614-28-2.

Reference:
Patent; ARDELYX, INC.; CHAO, Jianhua; (231 pag.)WO2019/55808; (2019); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Adding some certain compound to certain chemical reactions, such as: 455-68-5, name is Methyl 3-fluorobenzoate, 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 455-68-5. 455-68-5

REFERENCE EXAMPLE 68 Dimethyl 2-m-fluorophenyl-2-oxoethylphosphonate (68) STR87 To a stirred solution of dimethyl methylphosphonate (10.1 g, 81.2 mmol) in 100 ml of anhydrous THF was added dropwise n-butyl lithium (1.58N, 51.4 ml, 81.2 mmol) at -78¡ã C. under argon atmosphere. After 30 minutes, methyl m-fluorobenzoate (5.0 g, 32 mmol) was further added dropwise and the mixture was stirred for 30 minutes. The reaction solution was allowed to warm to 0¡ã C., diluted with 4.9 ml of acetic acid and 10 ml of water, and concentrated. 30 ml of water was added to the residue and the mixture was extracted with ethyl acetate (50 ml*2). The combined ethyl acetate layers were washed with water (20 ml*1) and brine (20 ml*1), dried over anhydrous sodium sulfate, and concentrated. The residue was distilled under reduced pressure to give an oil of dimethyl 2-m-fluorophenyl-2-oxo-ethylphosphonate (6.6 g, 26.8 mmol, yield 83.8percent, b.p. 132¡ã-134¡ã C./0.17 mmHg), which was assigned the structure by the following data: IR(Liquid film method): 3450, 3060, 2940, 2840, 1680, 1580, 1475, 1430, 1400, 1290, 1260, 1190, 1110, 1055, 1030, 870, 825, 790, 760, 710, 665 cm-1. NMR (90 MHz, CDCl3, delta): 3.62(2H, d, J=22.6 Hz), 3.79(6H, d, J=11.4 Hz), 7.15-7.9(4H, m).

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 Methyl 3-fluorobenzoate.

Reference:
Patent; Toray Industries, Inc.; US4775692; (1988); A;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

110-42-9, 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. 110-42-9 name is Methyl decanoate, 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.

EXAMPLE 7 13.5 g (0.083 mole) of diethylene glycol monobutyl ether was added dropwise to a mixture consisting of 1.6 g (0.042 mole) of sodium borohydride, 10 ml of xylene and 5 g (0.027 mole) of methyl caprate at 95 C. over two hours while agitating the mixture. Subsequently, the mixture was agitated at the same temperature for two hours. After cooling to room temperature, the mixture was neutralized with dilute sulfuric acid. As a result, n-decanol was obtained in 98% yield.

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

Reference:
Patent; Kao Corporation; US5196601; (1993); A;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

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. 89-91-8, name is Methyl 2,2-dimethoxyacetate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. 89-91-8

Method 1; Ethyl 4,4-dimethoxy-3 -oxobutanoate; To a solution of dimethoxy methyl acetate (25 g, 0.19 mol) in EtOAc (75 ml), was added sodium hydride (8.5 g, 0.21 mol) in portions. After all the sodium hydride was added, the mixture was set to reflux for 10 hours. The reaction mixture was poured onto cold water followed by pH adjustment to 3-4 using 3N HC1 solution. The layers were separated and the organic layer was dried, filtered, and concentrated in vacuo to afford 34 g (96% crude recovery) of the title compound, which was used further without purification.

The synthetic route of 89-91-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2006/8523; (2006); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

108928-00-3, A common compound: 108928-00-3, name is Ethyl 2,4-difluorobenzoate, 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 30A ethyl 2-(1H-indol-5-yloxy)-4-fluorobenzoate Ethyl 2,4-difluorobenzoate (1.14 g), K3PO4 (1.30 g) and 5-hydroxyindole (0.90 g) were stirred at 110 C. in diglyme (12 mL) for 24 hours. The reaction was cooled and poured into ether. The solution was washed three times with 1M aqueous NaOH solution, and brine, and dried over Na2SO4. The solution was then filtered, concentrated, and the crude product was chromatographed on silica gel with 20% ethyl acetate/hexanes.

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 2,4-difluorobenzoate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ABBOTT LABORATORIES; US2010/184750; (2010); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

87-13-8, Name is Diethyl 2-(ethoxymethylene)malonate, 87-13-8, 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.

A mixture of aniline (25.6 g, 0.28 mol) and diethyl 2-(ethoxymethylene)malonate (62.4 g, 0.29 mol) was heated at 140-150 C. for 2 h. The mixture was cooled to room temperature and dried under reduced pressure to afford 2-phenylaminomethylene-malonic acid diethyl ester as a solid, which was used in the next step without further purification. 1H NMR (d-DMSO) delta 11.00 (d, 1H), 8.54 (d, J=13.6 Hz, 1H), 7.36-7.39 (m, 2H), 7.13-7.17 (m, 3H), 4.17-4.33 (m, 4H), 1.18-1.40 (m, 6H).

Statistics shows that Diethyl 2-(ethoxymethylene)malonate is playing an increasingly important role. we look forward to future research findings about 87-13-8.

Reference:
Patent; Vertex Pharmaceuticals Incorporated; US2012/309758; (2012); A1;,
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 541-16-2 as follows. 541-16-2

General procedure: alpha,beta-Unsaturated aldehyde (3.0 mmol) and malonate (3.0 mmol) were added into asolution of TiCl4 (6.0 mmol) in CCl4 (2.0 mL) and THF (10 mL) at 0 C, Then, pyridine (0.96 mL, 12.0 mmol) in THF (2 mL) was added dropwisely over 1 h. The resulting mixture was stirred at room temperature overnight. After quenched with water, the mixture was extracted with ethyl acetate, dried over Na2SO4, filtered and concentrated under vacuum. The residue was purified by silica gel chromatography with hexane/ethyl acetate = 20/1 to afford the product.

According to the analysis of related databases, 541-16-2, the application of this compound in the production field has become more and more popular.

Reference:
Article; Wei, Xu; Lu, Junzhu; Duan, Wei-Liang; Synthesis; vol. 48; 23; (2016); p. 4155 – 4160;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 349-43-9, name is Ethyl 2-fluoropropionate, 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 349-43-9, 349-43-9

Add 12.0 g (0.1 mol) to a 250 ml four-necked flask with a condenserEthyl 2-fluoropropionate,240g of carbon tetrachloride,24.0 g (0.15 mol) of bromine,20.2 g (0.15 mol) of sulfuryl chloride,0.6g azoisobutyronitrile,StirThe reaction was carried out by heating to 70 ¡ãC.After 10 h, the conversion of methyl 2-fluoropropionate was 98.2percent.The selectivity to ethyl 2-fluoro-2-bromopropionate was 88.4percent.

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

Reference:
Patent; Juhua Group Technology Center; Ye Lifeng; Wang Shuhua; (5 pag.)CN104892409; (2018); B;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics