Tag: M.W=100-200

Synthetic Route of 3697-68-5, 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. 3697-68-5 name is Ethyl 1-(hydroxymethyl)cyclopropanecarboxylate, 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.

To a solution of ethyl 1-(hydroxymethyl)cyclopropane-1-carboxylate (5.0 g, 34.7 mmol) in dichloromethane (40 mL) and triethylamine (10.5 g, 104 mmol) was added methanesulfonyl chloride (3.66 mL, 47 mmol). The mixture was stirred at 0 C. for 2 h and diluted with dichloromethane (50 mL). The solution was then washed with citric acid (2*40 mL), brine (15 mL), dried over sodium sulfate and concentrated under reduced pressure. The residue was purified by column chromatography (silica gel, 100-200 mesh, 0 to 20% ethyl acetate in petroleum ether) to give ethyl 1-(methylsulfonyloxymethyl)cyclopropanecarboxylate (3.0 g, 39%) as a white solid. 1H NMR (400 MHz, CDCl3) delta 4.34-4.30 (m, 2H), 4.20-4.13 (m, 2H), 3.08 (s, 3H), 1.45-1.41 (m, 2H), 1.29-1.24 (m, 3H), 1.07-1.03 (m, 2H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Ethyl 1-(hydroxymethyl)cyclopropanecarboxylate, and friends who are interested can also refer to it.

Reference:
Patent; Genentech, Inc.; Patel, Snahel; Hamilton, Gregory; Stivala, Craig; Chen, Huifen; Daniels, Blake; US2019/127382; (2019); A1;,
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Adding a certain compound to certain chemical reactions, such as: 57486-67-6, name is Methyl 2-(2-fluorophenyl)acetate, 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 57486-67-6, HPLC of Formula: C9H9FO2

A solution of methyl 2-(2- fluorophenyl)acetate (6.373 g, 37.89 mmol) and methyl iodide (5.90 mL, 94.8 mmol, 2.5 equiv) in anhydrous THF (25 mL) was treated portionwise with sodium hydride (60% suspension in mineral oil, 3.32 g, 83.0 mmol, 2.2 equiv) at 0 C, warmed to room temperature and reacted for 24 h. The reaction mixture was transferred into a separatory funnel with ice/water and acidified with 1.0 M HC1 (30 mL). The product was extracted with ethyl acetate (3 x 30 mL). The combined organic layers were washed brine, filtered through cotton, and concentrated under reduced pressure to yield light yellow oil. The oil was dissolved in 16 mL of l,4-dioxane and 19.0 mL of 6.0 M NaOH (113.7 mmol, 3.0 equiv) was added. The mixture was heated at 95 C for 24 h. 30 mL of 3.0 M HC1 was added and the mixture was extracted with dichloromethane (3 x 20 mL). Combined organic fractions were washed with brine (30 mL), filtered through cotton and concentrated under reduced pressure to yield a crude mixture which was purified by flash chromatography (hexanes/ethyl acetate), 5.799 g of 2-methyl-2-(2-fluorophenyl)propanoic acid (31.83 mmol, 84% over two steps).

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; UNIVERSITY OF HOUSTON SYSTEM; DUBROVSKIY, Anton; KRIVOSHEIN, Arcadius, V.; (41 pag.)WO2019/99760; (2019); A1;,
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Adding a certain compound to certain chemical reactions, such as: 27798-60-3, name is Methyl 2-Methoxyphenylacetate, 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 27798-60-3, Application In Synthesis of Methyl 2-Methoxyphenylacetate

General procedure: The methyl arylacetate (1 equiv.) and p-ABSA (1.3 equiv.) were dissolved in acetonitrile and cooled to 0 C using an ice bath under an argon atmosphere. 1,8-Diazabicycloundec-7-ene (DBU, 1.3 equiv.) was then added to the stirring mixture over the course of 5 minutes. After the addition of the DBU, the reaction mixture continued to stir at 0 C for an additional 15 minutes. Once this allotted time had passed, the ice bath was removed and the reaction mixture was stirred for 24 hours at room temperature. The resulting orange solution was quenched with saturated NH4Cl and the aqueous layer was extracted with diethyl ether (3x). The organic layer was then washed with deionized H2O to remove any residual salts. The combined organic layers were dried over MgSO4 and filtered. The organic layer was then concentrated under reduced pressure. The residue was purified via flash chromatography on silica gel (10:1 Hexanes:EtOAc).

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; Chepiga, Kathryn M.; Qin, Changming; Alford, Joshua S.; Chennamadhavuni, Spandan; Gregg, Timothy M.; Olson, Jeremy P.; Davies, Huw M.L.; Tetrahedron; vol. 69; 27-28; (2013); p. 5765 – 5771;,
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Adding a certain compound to certain chemical reactions, such as: 56741-34-5, name is Methyl 5-amino-2-fluorobenzoate, 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 56741-34-5, Quality Control of Methyl 5-amino-2-fluorobenzoate

Step C : Methyl 5-amino-2-fluorobenzoate (5.21g, 30. 8MMOL) was added to a solution of concentrated sulfuric acid (45mL) in water (110ML). The resulting mixture was heated at 80C for 20min then cooled to 0C and treated dropwise with a solution of NaNO2 (2.34g, 33. 9MMOL) in lOmL of water. After stirring for 30MIN, a solution OF KI (7.16g, 43. 1MMOL) in 20mL of water was added. The reaction mixture was then warmed to rt and stirred overnight under a nitrogen atmosphere. Then the reaction mixture was stirred at 70C for 15MIN, cooled to rt, and extracted twice with ether. The combined ethereal layers were washed four times with water, once with brine, dried over anhydrous MgSO4, filtered, and concentrated. Purification by flash chromatography (silica, 10% ethyl ACETATE/HEXANES) provided methyl 2-FLUORO-5-IODOBENZOATE. LH NMR (500 MHz, CDC13) 8 8.25 (dd, 1H), 7.82 (M, 1H), 6.94 (dd, IH), 3.95 (s, 3H). ESI-MS calc. for C8H6FI02 : 280; Found: 281 (M+H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Methyl 5-amino-2-fluorobenzoate, and friends who are interested can also refer to it.

Reference:
Patent; MERCK & CO., INC.; WO2004/92124; (2004); A2;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Synthetic Route of 35180-01-9,Some common heterocyclic compound, 35180-01-9, name is Chloromethyl isopropyl carbonate, molecular formula is C5H9ClO3, 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 1000 ml reaction flask by adding 400 ml acetonitrile, 50mlNMP and 40g tynofovir a water composition, stirring is opened, to control the temperature to 20 C dropping under 67g triethylamine, drops to continue dropping 100g chloro methyl isopropyl carbonate, the reaction system after the dipping temperature is increased to 50 C insulation reaction 8 hours, the detection reaction monoester less than 10%, in the reaction liquid 40 C the following concentrate under reduced pressure until there is no liquid can flow out, in the concentrated residual liquid by adding 500 ml ethyl acetate, 200ml6% of sodium bicarbonate solution, stir layered after extraction, the organic phase continue to use 200 ml purified water washing two times, the resulting organic phase after drying by anhydrous sodium sulfate concentrated under reduced pressure to dry, the resulting concentrated residual liquid directly used for the next reaction.

The synthetic route of 35180-01-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Suzhou Homesun Pharmaceutical Co., Ltd.; Fan, Chao; (7 pag.)CN105418684; (2016); A;,
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Related Products of 606-45-1, 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. 606-45-1, name is Methyl 2-methoxybenzoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

In cyclohexane: To a suspension of AlI3 (5.5 mmol, 1.0 eq.) in cyclohexane (40 mL) was added methyl o-anisate (4, 0.915 g, 5.5 mmol). After stirring for 1 d under reflux, themixture was acidified with dilute HCl (2 M, 10 mL), extracted with EA (50 mL ¡Á 3). The combined organic phases were combined, washed with Na2S2O3, and dried over MgSO4.After filtration, the organic solvents were removed by a rotary evaporator, and the residue was purified through column chromatography (eluent: PE/EA 3:1) to afford 8 (0.661g, 86%) as a white solid.

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

Reference:
Article; Sang, Dayong; Yi, Cuicui; He, Zhoujun; Wang, Jiahui; Tian, Juan; Yao, Ming; Shi, Hong; Tetrahedron Letters; vol. 59; 15; (2018); p. 1469 – 1472;,
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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. 924-99-2, name is Ethyl 3-(dimethylamino)acrylate, A new synthetic method of this compound is introduced below., Recommanded Product: 924-99-2

6.1.1 Ethyl 2-(2,4-difluorobenzoyl)-3-(dimethylamino)acrylate (8) A mixture of substituted 2, 4-difluorobenzoyl chloride (3.19 g, 18.1 mmol), ethyl 3-(dimethylamino)acrylate (2.59 g, 18.1 mmol, 1.0 equiv), and triethylamine (2.74 g, 27.1 mmol, 1.5 equiv) in toluene (30 mL) was stirred at 90 C for 4 h. After cooling, the reaction mixture was filtered. The filtrate was concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (petroleum ether/ethyl acetate 2:1 to 1:2, v/v) to give the desired product 8 as yellow oil. Yield 65%; 1H NMR (400 MHz, CDCl3) delta 7.79 (s, 1H), 7.62-7.68 (m, 1H), 6.89-6.93 (m, 1H), 6.74-6.80 (m, 1H), 4.03-3.98 (q, J = 7.2 Hz, 2H), 3.31 (s, 3H), 2.89 (s, 3H), 0.95-0.99 (t, J = 7.2 Hz, 3H).

The synthetic route of 924-99-2 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Mao, Tian-Qi; He, Qiu-Qin; Wan, Zheng-Yong; Chen, Wen-Xue; Chen, Fen-Er; Tang, Gang-Feng; De Clercq, Erik; Daelemans, Dirk; Pannecouque, Christophe; Bioorganic and Medicinal Chemistry; vol. 23; 13; (2015); p. 3860 – 3868;,
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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. 10047-10-6, name is Methyl 2-aminopentanoate hydrochloride, A new synthetic method of this compound is introduced below., COA of Formula: C6H14ClNO2

(a) To a stirred solution of 7.36 ml (84.9 mmol) of chlorosulfonyl isocyanate in 150 ml of methylene chloride was added benzyl alcohol (8.82 ml, 84.7 mmol) at 0-5 C. After stirring the above solution for 1.5 hours at this temperature, a solution of 15.62 g (93.25 mmol) of 2-amino-pentanoic acid methyl ester hydrochloride in 500 ml of methylene chloride containing triethylamine (25.54 g, 0.2528 mol) was added at 0-5 C., and the resulting mixture was stirred overnight allowing the mixture to warm to room temperature. The reaction mixture was poured into 600 ml of 10% aq. HCl solution, saturated with sodium chloride, and the organic layer was separated. The aqueous layer was extracted with methylene chloride/ethyl acetate (4:1, 2*200 ml) and the combined organic layer was washed with brine, dried and concentrated in vacuo to yield 28.2 g (87.6%) of 2-(N-carbobenzyloxyaminosulfonyl) aminopentanoic acid methyl ester (Formula XIV: R=CH3, R1 =H; R2 =propyl; R3 =H) as a solid, m.p. 76-78 C.

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; Sterling Winthrop Inc.; US5494925; (1996); A;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 27741-65-7, name is Ethyl 2-cyclobutylideneacetate, 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 27741-65-7, Application In Synthesis of Ethyl 2-cyclobutylideneacetate

Step 2: 6′-Hydroxy-5,7′-dimethylspiro[cyclobutane-1,2′-thiochromen]-4′(3’H)-one To a solution of 4-mercapto-2,6-dimethylphenol (2.5 g) in anhydrous methanol (40 mL) containing trimethyl orthoformate (3 mL), was added cyclobutylidene-acetic acid ethyl ester (7.6 g) and then 5 drops of concentrated sulfuric acid. The solution was deoxygenated by bubbling with nitrogen, and was allowed to reflux for 4 days. The mixture was concentrated, washed with saturated NaHCO3 and extracted with ethyl acetate. After concentrated in vacuo, the residue was purified by flash chromatography eluted with 10-20% ethyl acetate in hexane to give 3.1 g of methyl {1-[(4-hydroxy-3,5-dimethylphenyl)thio]cyclobutyl}acetate as a white solid. The above addition product (3.1 g) was suspended in 200 mL of 1N NaOH in MeOH and water (1:1, v/v), and the mixture was allowed to stir for 1 hour. The reaction mixture was then acidified with 1N HCl and extracted 3 times with ethyl acetate. The organic layer was washed with water and dried over anhydrous Na2SO4, and concentrated in vacuo.

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

Reference:
Patent; Galileo Pharmaceuticals, Inc.; US2006/128790; (2006); 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. 174403-69-1, name is Methyl 4-fluoro-2-methylbenzoate, This compound has unique chemical properties. The synthetic route is as follows., Safety of Methyl 4-fluoro-2-methylbenzoate

Example 146 Preparation of 2-carbomethoxy-5-fluorobenzyl bromide STR222 A suspension of the compound of Example 145 (5.1 g, 30 mmol), N-bromosuccinimide (5.4 g, 30 mmol) and benzoyl peroxide (0.073 g, 0.30 mmol) in carbon tetrachloride (115 mL) was refluxed for 18 h. The reaction mixture was cooled to 0 C., filtered, and the precipitate was washed with diethyl ether. The solvent was removed in vacuo to afford 7.02 g (94% crude yield) of the title compound, contaminated with a small amount of succinimide. Rf =0.48 20% ethyl acetate/hexanes.

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 174403-69-1.

Reference:
Patent; Corvas International, Inc.; US6011158; (2000); A;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics