Tag: M.W=100-200

Synthetic Route of 2969-81-5, 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. 2969-81-5, name is Ethyl 4-bromobutyrate, This compound has unique chemical properties. The synthetic route is as follows.

To a solution of 4-chlorophenol (10 g, 77.784 mmol, 1 equiv) in N,N- dimethylformamide (100 mL) was added anhydrous potassium carbonate (21 .5 g, 1 16.6 mmol, 2 equiv) and ethyl 4-bromobutanoate (16.7 mL, 1 16.677 mmol, 1 .5 equiv). The reaction mixture was heated to 140 C and stirred for 4 h. The progress of the reaction was monitored by TLC. After completion of reaction, the reaction mixture was allowed to cool to 27 C, filtered the solid and washed with ethyl acetate (700 mL). The filtrate was washed with water (2 x 200 mL), brine solution (100 mL), dried over anhydrous sodium sulphate, filtered and concentrated under reduced pressure to give the crude product. The crude product was purified by silica gel column chromatography using 10 % ethyl acetate in hexane as eluent to obtain ethyl 4-(4-chlorophenoxy)butanoate (17.0 g, 89 % yield) as white solid. LCMS (ES) m/z = 243.1 [M+H]+. NMR (400 MHz, CDCI3): delta ppm 1 .25 (t, J = 7.2 Hz, 3 H), 2.06 – 2.12 (m, 2 H), 2.49 (t, J = 7.6 Hz, 2 H), 3.97 (t, J = 6.0 Hz, 2 H), 4.1 1 – 4.17 (m, 2 H), 6.80 (d, J = 8.8 Hz, 2 H), 7.21 (d, J = 8.8 Hz, 2 H).

The chemical industry reduces the impact on the environment during synthesis Ethyl 4-bromobutyrate. I believe this compound will play a more active role in future production and life.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; AXTEN, Jeffrey; CHEUNG, Mui; DEAN, Anthony W.; DEMARTINO, Michael P.; EIDAM, Hilary Schenck; KETHIRI, Raghava Reddy; KALITA, Biswajil; KRISTAM, Rajendra; (162 pag.)WO2017/212423; (2017); A1;,
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Application of 14062-29-4, The chemical industry reduces the impact on the environment during synthesis 14062-29-4, name is Ethyl 2-(3-chlorophenyl)acetate, I believe this compound will play a more active role in future production and life.

EXAMPLE 23 6-(3-Chlorobenzyl)-1-(2-methoxyphenyl)-1,5-dihydro-4H-pyrazolo[3,4-d]pyrimidin-4-one In analogy to the preparation of Example 9, 180 mg (76% of theory) of the desired product are obtained as a colourless solid starting from 0.15 g (0.65 mmol) of 5-amino-1-(2-methoxyphenyl)-1H-pyrazole-4-carboxamide (Example 31A), 0.394 g (98% purity, 1.94 mmol) of ethyl (3-chlorophenyl)acetate and 0.129 g (3.23 mmol) of 60% sodium hydride. m.p.: 196 C. MS (ESI pos): m/z=367 (M+H)+ 1H-NMR (300 MHz, DMSO-d6): delta=3.7 (s, 3H), 3.9 (s, 2H), 7.0-7.6 (m, 8H), 8.2 (s, 1H), 12.4 (s, 1H) ppm.

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-(3-chlorophenyl)acetate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Bayer HealthCare AG; US2007/161662; (2007); A1;,
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Electric Literature of 1949-51-5, A common heterocyclic compound, 1949-51-5, name is Ethyl 3,5-diaminobenzoate, molecular formula is C9H12N2O2, 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.

In a round-bottom flask placed in an ice bath, 11 (1.0 eq.) was solubilized in a mixture of dioxane and water (2:1), followed by addition of triethylamine (Et3N; 2.2 eq.). Next, di-tert-butyl-dicarbonate ((Boc)2O; 1.0 eq.) was solubilized in a small amount of dioxane and added dropwise to the mixture. The reaction was stirred at room temperature overnight. The solvents were evaporated and the crude was dissolved in ethyl acetate and washed with 10% aqueous solution of citric acid and water. The collected organic phases were dried over MgSO4, concentrated in vacuo and purified by column chromatography (dichloromethane/acetonitrile 95/5-90/10). The desired product formed pale-yellow crystals (80% yield).

The synthetic route of 1949-51-5 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Czescik, Joanna; Zamolo, Susanna; Darbre, Tamis; Mancin, Fabrizio; Scrimin, Paolo; Molecules; vol. 24; 15; (2019);,
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Electric Literature of 10076-48-9, These common heterocyclic compound, 10076-48-9, name is Methyl 2,2-dimethoxypropanoate, 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 5 Methyl 2,2-dimethoxypropionate (66.9 g, 0.45 mol), hydroquinone (0.1 g), quinoline (74.5 g, 0.58 mol) (dried over potassium hydroxide), and acetyl chloride (48.4 g, 0.62 mol) were combined at 5-10 C. in a Fischer-Porter bottle. Powdered potassium hydroxide (0.45 g, 0.008 mol) was added. The reaction mix formed a thick white slurry. The bottle was sealed, stirred with a magnetic stirrer, and placed in a 122 C. oil bath. After three hours the bottle pressure was 19-22 psig. The reaction mixture was diluted with toluene and the quinoline hydrochloride was removed by filtration. The filtrate was concentrated and distilled to give methyl 2-methoxyacrylate (35 g, 68%): bp 35 C. (4 torr). This example demonstrates that methyl 2-methoxyacrylate can be prepared using superatmospheric pressure.

Statistics shows that Methyl 2,2-dimethoxypropanoate is playing an increasingly important role. we look forward to future research findings about 10076-48-9.

Reference:
Patent; Chevron Research Company; US4304928; (1981); A;,
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114312-57-1, name is Ethyl 3-fluoro-2-methylbenzoate, 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. HPLC of Formula: C10H11FO2

To a solution of 11 g of ethyl 3-fluoro-2-methylbenzoate in 300 ml of carbon tetrachloride is added 12 g of N-bromosuccinimide and the mixture is refluxed with heating for 12 hours. After cooling, the mixture is washed with water and a saturated saline solution and dried over magnesium sulfate and the solvent is distilled off under reduced pressure to give 13 g of ethyl 3-fluoro-2-bromomethylbenzoate. Mass spectrum m/z: 262, 260(M+).

The synthetic route of 114312-57-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Dainippon Pharmaceutical Co., Ltd.; US4889858; (1989); 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. 40637-56-7, name is Dimethyl 2-allylmalonate, A new synthetic method of this compound is introduced below., COA of Formula: C8H12O4

4.1.1 2-Allyl-2-methoxycarbonyl-malonic acid dimethyl ester (5) 13 At 0 C, to a suspension of NaH (60% in mineral oil) (5.85 g, 146.2 mmol, 1.5 equiv) in THF (150 mL), was added 4 (16.78 g, 97.4 mmol) and the mixture was warmed to rt and stirred during 1 h. Then, freshly distilled ClCO2Me (20 mL, 258.0 mmol, 2.6 equiv) was slowly added at 0 C and the solution was warmed to rt and stirred during 2 h. The reaction mixture was diluted in diethyl ether and washed with saturated aqueous solution of ammonium chloride and brine, dried over MgSO4, filtered, and concentrated. Pure compound 5 (20.41 g, 88.6 mmol, 91%) was obtained as a colorless oil. 1H NMR (CDCl3, 200 MHz) delta 5.95-5.77 (ddt, J=17.2; 10.3 and 7.4 Hz, 1H, H2C=CHCH2); 5.09 (dd, J=17.2 and 1 Hz, 1H, HC=CHtrans); 4.99 (dd; J=10.3 and 1 Hz, 1H, HC=CHcis); 3.70 (s, 9H, CO2CH3); 2.78 (d, J=7.4 Hz, 2H, H2C=CHCH2). 13C NMR (CDCl3, 50 MHz) delta 166.9 (CO2CH3); 132.4 (H2C=CHCH2); 119.4 (H2C=CHCH2); 65.7 (C(CO2CH3)3); 53.1 (CO2CH3); 37.6 (H2C=CHCH2). IR (neat), cm-1: 2900; 1740; 1460; 1370; 1230. Anal. for C10H14O6 (M=230.22 g mol-1): calcd (%) : C=52.17; H=6.13. found (%) : C=52.06; H=6.32.

The synthetic route of 40637-56-7 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Agarwal, Jyoti; Commandeur, Claude; Malacria, Max; Thorimbert, Serge; Tetrahedron; vol. 69; 45; (2013); p. 9398 – 9405;,
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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 210530-71-5 as follows. Recommanded Product: Methyl 2-(3,4-difluorophenyl)acetate

Sodium hydride (containing mineral oil at 40%, 0.48 g) was added to a solution of methyl (3,4-difluorophenyl)acetate (CAS No.210530-71-5, 2.04 g) in DMF (30 mL) at 0 C., and the reaction solution was stirred at room temperature for 10 minutes. 1-chloro-3-iodopropane (1.3 mL) was added to the reaction solution at 0 C., and the reaction solution was stirred at room temperature for two hours. A saturated ammonium chloride solution was added to the reaction solution, followed by extraction with ethyl acetate. The resulting extract washed with a saturated sodium chloride solution. The resulting organic layer was dried over magnesium sulfate and then concentrated under reduced pressure. Hydrazine monohydrate (5.5 g) was added to a solution of the resulting residue in ethanol (50 mL) at room temperature, and the reaction solution was stirred at 80 C. for seven hours. The reaction solution was left to cool to room temperature and concentrated under reduced pressure. A saturated sodium bicarbonate solution was added to the residue, followed by extraction with chloroform. The resulting extract was dried over magnesium sulfate and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (elution solvent:heptane-ethyl acetate system, then ethyl acetate-methanol system) to obtain 1.42 g of the title compound. The property values of the compound are as follows. ESI-MS; m/z 227 [M++H]. 1H-NMR (CDCl3) delta (ppm): 1.84-2.06 (m, 3H), 2.10-2.21 (m, 1H), 3.53-3.71 (m, 3H), 4.59 (brs, 2H), 6.89-6.95 (m, 1H), 6.97-7.05 (m, 1H), 7.06-7.26 (m, 1H).

According to the analysis of related databases, 210530-71-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Eisai R&D Management Co., Ltd.; US2007/219181; (2007); A1;,
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Application of 14062-24-9, These common heterocyclic compound, 14062-24-9, name is Ethyl 4-chlorophenylacetate, 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: Sodium hydride (1.33 ml, 2.61 mmol) was added dropwise to a solution of phenyl acetonitrile (1.0 g, 8.5 mmol)) in anhydrous THF (30 mL), the mixture was stirred at R.T. for30 minutes, followed by adding a solution of ethyl 4-chlorobenzoate (1.78 g, 10.2 mmol) in anhydrous THF (30mL). The mixture was refluxed till the reaction was finished.The result mixture was quenched with water and extracted with ether. The aqueous layer was acidified with 10% HCl to filter out the white precipitation, which was recrystallized with ether to give a white solid. Yield: 76%-80%.

The synthetic route of 14062-24-9 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Hu, Chunqi; Shen, Jianfeng; Du, Wenting; Letters in drug design and discovery; vol. 14; 2; (2017); p. 151 – 158;,
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Adding a certain compound to certain chemical reactions, such as: 41658-03-1, name is Ethyl 3-bromopropiolate, 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 41658-03-1, COA of Formula: C5H5BrO2

General procedure: A solution of 3-phenyl sydnone (3, 100 mg, 1.0 equiv) in 4.0 mL p-xylene was added ethyl 3-bromopropynoate (120 mg, 1.05 equiv) and heated to reflux for 5 h. The residue was cooled down and added 2-aminophenylboronic acid pinacol ester (820 mg, 1.1 equiv), Pd(PPh3)4 (39 mg, 0.1 equiv), K2CO3 (2 mL, 2 M aqueous solution), and EtOH (4.0 mL). The reaction mixture was stirred at reflux for 24 h. When the reaction was completed, the reaction mixture was concentrated under reduced pressure to remove p-xylene and EtOH. The residue was added with 20 mL water, and extract with EtOAc (40 mL). The organic layer was filtered to remove the insoluble substances, then dried over MgSO4, filtered, and concentrated under reduced pressure. The residue solution was purified by column chromatography on silica gel to give the corresponding 2-arylpyrazolo[3,4-c]quinolin-4(5H)-one 1b-e and 2-arylpyrazolo[4,3-c]quinolin-4(5H)-one 2b-e products in 27-32% and 39-43% yields, respectively.

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

Reference:
Article; Chang, En-Chiuan; Wen, Ya-Lan; Chang, Chun-Hsi; Shen, Yun-Hwei; Wen, Shaw-Bing; Yeh, Mou-Yung; Wong, Fung Fuh; Tetrahedron; vol. 68; 29; (2012); p. 5920 – 5924;,
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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. 18595-18-1, name is Methyl 3-amino-4-methylbenzoate, A new synthetic method of this compound is introduced below., COA of Formula: C9H11NO2

In a 10 mL pear-shaped flask, 6,7-dimethoxy-2-oxo-1,2,3,4-tetrahydroquinoline-3-carboxylic acid (92.0 mg, 0.366 mmol, 1.00 eq) (from Example 71, Step D supra) and methyl 3-amino-4-methylbenzoate (90.7 mg, 0.549 mmol, 1.50 eq) (TCI) were combined in DMF (1.1 mL). Triethylamine (0.255 mL, 1.83 mmol, 5.00 eq) and then HATU (209 mg, 0.540 mmol, 1.50 eq) (Aldrich) were added resulting in a yellow solution. After stirring for 3 hours at room temperature the reaction was diluted with EtOAc, extracted twice with water and once with brine and then concentrated. The solid residue was triturated with water and then with hot EtOAc to give 3-[(6,7-dimethoxy-2-oxo-1,2,3,4-tetrahydro-quinoline-3-carbonyl)-amino]-4-methyl-benzoic acid methyl ester. (Yield 97.2 mg, 0.244 mmol, 66.6%). HR-MS (ES+) m/z Calculated for C21H22N2NaO6 ([M+Na]+): 421.1370. Found: 421.1371.

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; Dominique, Romyr; Luk, Kin-Chun; Qiao, Qi; Rossman, Pamela Loreen; US2012/184548; (2012); A1;,
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