Tag: M.W=100-200

Electric Literature of 23426-63-3,Some common heterocyclic compound, 23426-63-3, name is Methyl 2-bromo-2-methylpropanoate, molecular formula is C5H9BrO2, 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.

Intermediate 2: Methyl 2-(l,2,3,4-tetrahydroisoquinolin-6-yloxy)-2- methylpropanoate.’ .[0060] Step A: 6-Hydroxyisoquinoline (1.0 g, 6.9 mmol) and methyl 2- bromoisobutyrate (3.4 mL, 27.5 mmol) are dissolved in dry DMF (20 mL). Powdered potassium carbonate (3.8 g, 27.5 mmol) is added and the mixture is heated at 100 C for 16 h. The mixture is cooled, diluted- with ethyl acetate (40 mL), washed with water (3 x 50 mL) and brine (50 mL). The organic layer is dried (MgSO4), filtered, evaporated and purified by silica gel chromatography (0-100% gradient, ethyl acetate in hexanes) to provide methyl 2-(isoquinolin-6-yloxy)-2-methylpropanoate 1 (1.25 g, 74%) as a colorless oil. MS calcd. for Ci4Hi6NO3 (TVB-H+) 246.1, found 246.1.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Methyl 2-bromo-2-methylpropanoate, its application will become more common.

Reference:
Patent; IRM LLC; WO2007/89557; (2007); A2;,
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Electric Literature of 1865-29-8,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.

The title compound was synthesized according to a literature method (Whitman Tetrahedron 1985, 41, 1183). To a mixture of 2-phenylacrylic acid methyl ester (7.92g, 45 mmol) in 60 ml of methylene chloride was added mCPBA (13. Ig, 58.5 mmol) and the reaction was stirred at 450C overnight. The reaction mixture was then filtered and the solid was washed with methylene chloride. The filtrate was washed three times with 50 ml of equal parts solution consisting of saturated Na2S2O3 and saturated NaHCO3. The organic layer was washed with water and brine, dried over MgSO4, and concentrated under reduced pressure to afford the title compound in greater than 95% purity according to 1H NMR (85% yield). 1H NMR (CDCl3, 300MHz) delta: 7.50 -7.30 (m, 5H), 4.22 (q, J= 7.2 Hz, 2H), 3.40 (d, J, = 7.1 Hz, IH), 2.95 (d, J= 7.1Hz, IH), 1.26 (t, J=7.2Hz, 3H) ppm.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Methyl 2-phenylacrylate, its application will become more common.

Reference:
Patent; YUDIN, Andrei, K.; HILI, Ryan; WO2008/46232; (2008); 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. 15224-11-0, name is Ethyl 2-(hydroxymethyl)cyclopropanecarboxylate, A new synthetic method of this compound is introduced below., Quality Control of Ethyl 2-(hydroxymethyl)cyclopropanecarboxylate

EXAMPLE 40 ethyl 2-{[4-chloro-2-({[(5-cyano-2-pyrazinyl)amino]carbonyl}amino)phenoxy]methyl}cyclopropanecarboxylate The desired product (2.5 mg, 6%) was prepared by substituting ethyl 2-(hydroxymethyl)cyclopropanecarboxylate (14.4 mg, 0.10 mmol) for 2-cyclohexen-1-ol in Example 1. MS (ESI(-)) m/z 414 (M-H)-; 1H NMR (500 MHz, DMSO-d6) delta 10.95 (s, 1H), 10.20 (br s, 1H), 8.91 (s, 1H), 8.77 (s, 1H), 8.24-8.28 (m, 1H), 7.04-7.11 (m, 2H), 4.12-4.18 (m, 1H), 3.96-4.08 (m, 3H), 1.82-1.92 (m, 1H), 1.73-1.79 (m, 1H), 1.10-1.19 (m, 4H), 1.02-1.08 (m, 1H).

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; Li, Gaoquan; Li, Qun; Li, Tongmei; Lin, Nan-Horng; Mantei, Robert A.; Sham, Hing L.; Wang, Gary T.; US2004/259885; (2004); A1;,
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Synthetic Route of 2065-23-8, The chemical industry reduces the impact on the environment during synthesis 2065-23-8, name is Methyl 2-phenoxyacetate, I believe this compound will play a more active role in future production and life.

167.87 g of 99% methyl phenoxyacetate (1 mol), 1.26 g of 99% zinc chloride and 1.68 g of 99% were sequentially added to a 500 mL four-necked flask.2,5-dichlorothiazole, 154.69 g of 99% chlorine (2.16 mol) was introduced at -20 C.After the heat preservation reaction for 30 minutes,Distilling and collecting fractions of 140-150 C under a pressure of 1 kpa,Methyl 2,4-dichlorophenoxyacetate236.21g, content 98.8%,The yield was 99.28% based on methyl phenoxyacetate.

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

Reference:
Patent; Shandong Runbo Biological Technology Co., Ltd.; Sun Guoqing; Hou Yongsheng; Zhang Liguo; Chi Zhilong; Hu Yishan; (12 pag.)CN108947807; (2018); 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. 609-08-5, name is Diethyl 2-methylmalonate, A new synthetic method of this compound is introduced below., Formula: C8H14O4

To a THF (0.5 M) solution of diethyl methylmalonate (1 eq.) was added sodium hydride (1.4 eq., 60% (w/w) dispersion in paraffin oil) in four equal portions, three to five minutes apart. The reaction was maintained at 0C for 15 mm, before it was allowed to warm to RT over 30 mm. After another 30 mm of stirring at RT, the mixture was re-cooled to 0C and then added N-fluorobenzenesulfonamide (1.1 eq.) in four equal portions. Stirring was continued at 0C for 30 mm and then at RT for 4 h, at which time it was determined to be >95% complete by ?H NMR. The reaction was then diluted with hexanes and vacuum filtered. The filter cake was washed further with hexanes and the product-containing filtrate was concentrated. More hexanes was added to induce further precipitation of unwanted- by-products and the suspension was filtered again. The filtrate thus obtained was then concentrated in vacuo to furnish a biphasic oil. The upper layer was determined to be paraffin oil and was discarded. The lower layer was the desired product (82% yield).

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 PATENT GMBH; JORAND-LEBRUN, Catherine; LAN, Ruoxi; CHEN, Austin; CLARK, Ryan C.; (268 pag.)WO2017/49068; (2017); 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. 10601-80-6, name is Ethyl 3,3-diethoxypropionate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. HPLC of Formula: C9H18O4

0463] To a solution of ethyl 3,3-diethoxypropanoate (20 g, 105 mmol) in water (80 ml) was added sodium hydroxide (5 g, 125 mmol, 1.2 eq). The resulting solution was stirred for 1 hour at 110 C. in an oil bath and then adjusted to pH 5 with aqueous hydrogen chloride (3N). The crude product was then extracted with tetrahydrofuran (3×80 ml) and the organic layers were combined, dried over anhydrous sodium sulfate, and filtered before being concentrated under vacuum. The crude residue was purified by silica gel chromatography using 3-50% ethyl acetate in petroleum ether to elute. The product-containing fractions were combined and concentrated under vacuum to afford 3,3-diethoxypropanoic acid as light yellow oil (12 g, 70%); 1H NMR (300 MHz, DMSO): delta 4.80-4.82 (t, J=5.7 Hz, 1H), 3.41-3.61 (m, 4H), 2.49 (d, J=5.7 Hz, 2H), 1.06-1.24 (m, 6H).

The synthetic route of 10601-80-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Merial Limited; Meng, Charles Q.; Long, Alan; Huber, Scot; Gurrala, Srinivas Reddy; Wilkinson, Douglas Edward; Pacofsky, Gregory; US2014/142114; (2014); A1;,
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Electric Literature of 56741-34-5, These common heterocyclic compound, 56741-34-5, name is Methyl 5-amino-2-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.

General procedure: To a solution of 11a (500 mg, 1.85 mmol) in acetone (10 mL) was added 12 (380 mg, 1.85 mmol) and pyridine (0.45 mL, 5.54 mmol).The mixture was stirred at 55 C for 1 h. The mixture was concentrated,diluted with ethyl acetate and washed with 1M HCl and brine twice.Then, the ethyl acetate layer was dried over anhydrous sodium sulfate andconcentrated to give the crude product. The crude product was purified bysilica column eluting with petroleum ether/ethyl acetate (5/1-2/1) to givethe desired product (0.33 g, yield 44.3%) as grey solid

Statistics shows that Methyl 5-amino-2-fluorobenzoate is playing an increasingly important role. we look forward to future research findings about 56741-34-5.

Reference:
Article; He, Yulong; Dou, Huixia; Gao, Dingding; Wang, Ting; Zhang, Mingming; Wang, Heyao; Li, Yingxia; Bioorganic and Medicinal Chemistry; vol. 27; 19; (2019);,
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Reference of 22223-49-0, 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 22223-49-0 as follows.

A mixture of 2-amino-3-methylbenzoic acid (15.2 g, 0.10 mol), dimethylformamide (333 mL) and CsCO3 (49 g, 0.15 mol) was stirred at room temperature for about 40 minutes before drop wise addition of iodomethane (14.2 g, 6.2 mL, 0.10 mol) in dimethylformamide (“DMF”) (115 mL). The mixture was stirred . at room temperature overnight. The mixture was diluted with water (1 L), and extracted with diethyl ether. The aqueous phase was back extracted with diethyl ether. The combined organic extracts were washed with saturated aqueous NaCI, dried over MgSO4, filtered and concentrated. The resultant material was dried at room temperature/0.5 mmHg to afford methyl 2-amino-3-methylbenzoate (17 g, 100%).To a solution methyl 2-amino-3-methylbenzoate (16.5 g, 0.10 mol) in CHCI3 (286 mL) was added acetic anhydride (23.5 g, 21.7 mL, 0.23 mol) so as to maintain the internal temperature <40 0C. The mixture was stirred at room temperature for 1 hour before addition of potassium acetate (2.94 g, 30 mmol) and isoamyl nitrite (25.8 g, 30 mL, 0.22 mol). The resultant mixture was heated at reflux overnight. To this was then added methanol (94 mL) and 6 N HCI (94 mL) and the mixture was stirred overnight. The reaction mixture was concentrated to provide an orange solid which was subsequently triturated with ethyl acetate and the solids were isolated by vacuum filtration. The solids were dried at room temperature/0.5 mmHg to afford methyl 1 H-indazole-7-carboxylate (15.4 g, 88%). -A solution of methyl 1 H-indazole-7-carboxylate (14.96 g, 84.9 mmol) in methanol (180 ml_) was cooled to 0 0C before addition of 29% aqueous potassium hydroxide (36 ml_). The ice bath was removed and the reaction mixture was stirred at room temperature overnight. The pH was adjusted to 5.5 using concentrated HCI. The volatiles were removed by vacuum filtration and the resultant material was suspended in water (100 mL) and ethyl acetate (200 mL). The resultant precipitate was isolated by vacuum filtration and rinsed with ethyl acetate. The solids were dried at room temperature/0.5 mmHg to afford the title compound (7.54 g, 55%).

According to the analysis of related databases, 22223-49-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; PFIZER PRODUCTS INC.; WO2008/65508; (2008); 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. 57625-74-8, name is Methyl 2-methyl-2-phenylpropanoate, This compound has unique chemical properties. The synthetic route is as follows., Application In Synthesis of Methyl 2-methyl-2-phenylpropanoate

General procedure: The ester II was added to a mixture of NaOH (2.0 M, 8 mL) and methanol (10 mL)and stirred overnight at 65 C. After removal of methanol in vacuo, the residue wasdiluted with water and extracted with EtOAc (10 mL × 3). Then the pH value of thewater layer was adjusted to 2.0 with HCl (2.0 M) and extracted with EtOAc (30 mL ×3). The combined organic phases were evaporated in vacuo to give the crudecarboxylic acid III, which was used directly for the next step without furtherpurification.

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 57625-74-8.

Reference:
Article; Zhou, Danni; Wang, Chunxia; Li, Mingliang; Long, Zheng; Lan, Jingbo; Chinese Chemical Letters; vol. 29; 1; (2018); p. 191 – 193;,
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Synthetic Route of 37746-78-4, These common heterocyclic compound, 37746-78-4, name is (E)-Ethyl 4-bromobut-2-enoate, 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.

General procedure: Amines 10a-f (1.0 equiv), N,N-diisopropylethylamine (1.5 equiv), ethyl (E)-4-bromobut-2-enoate(5, 1.3 equiv) and CH2Cl2 (25 mL) were placed in a round bottom flask and stirred at 20 C for1 h, under nitrogen. After completion of the reaction (TLC) the reaction mixture was extracted withNaHCO3 (3 30 mL) and water (1 30 mL). The organic phase was dried over Na2SO4 and thesolvent removed under reduced pressure to yield the crude product. The crude product was purifiedby silica gel column chromatography (9:1 hexanes:EtOAc).Ethyl (E)-4-(thiazolidin-3-yl)but-2-enoate (14a). 1.21 g (63 %) as a yellow oil.

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

Reference:
Article; Rodriguez-Lozada, Josue; Tovar-Gudino, Erika; Guevara-Salazar, Juan Alberto; Razo-Hernandez, Rodrigo Said; Santiago, Angel; Pastor, Nina; Fernandez-Zertuche, Mario; Molecules; vol. 23; 11; (2018);,
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