Tag: M.W=100-200

Synthetic Route of 27798-60-3,Some common heterocyclic compound, 27798-60-3, name is Methyl 2-Methoxyphenylacetate, molecular formula is C10H12O3, 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.

Preparation of methyl 2-(2-methoxyphenyl)-3-phenylpropanoate (27): A 50OmL round- bottom flask is charged with methyl 2-(2-methoxyphenyl)acetate (8.496 g, 47 mmol, leq) and THF (20OmL). The homogeneous mixture is cooled to 0 0C in an ice bath. Lithium diisopropyl amide (23.5mL of a 2.0M solution in heptane/THF) is added, maintaining a temperature less than 30C. The reaction is stirred 45 minutes at this reduced temperature. Benzyl bromide (5.6mL, 47mmol, leq) is added dropwise. The reaction is allowed to gradually warm to roomtemperature and is stirred for 18 hours. The reaction is quenched with IN HCl and extracted 3 times with equal portions of EtOAc. The combined extracts are washed with H2O and brine, dried over Na2SO4, filtered, and concentrated. The residue is purified over silica to afford 4.433g (35%) of the desired compound. ESI+ MS 293 (M+Na).

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-Methoxyphenylacetate, its application will become more common.

Reference:
Patent; AKEBIA THERAPEUTICS INC.; SHALWITZ, Robert; WO2011/5330; (2011); A1;,
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Synthetic Route of 3618-04-0,Some common heterocyclic compound, 3618-04-0, name is trans-Ethyl 4-hydroxycyclohexanecarboxylate, molecular formula is C9H16O3, 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 B Ethyl 4-oxocyclohexanecarboxylate Ethyl 4-hydroxybenzoate is reduced to ethyl 4-hydroxycyclohexanecarboxylate according to the procedure described in R. A. Finnegan and P. L. Bachman, Journal of Organic Chemistry, Volume 30, pages 4145-4150 (1965). The crude material obtained in this reduction (190 g) is dissolved in 1200 ml of reagent grade acetone. The solution is cooled to 0 C. and 152 ml of a 8 N chromic acid solution (prepared from concentrated sulfuric acid and chromium trioxide) is added dropwise to the mechanically stirred reaction mixture. Enough isopropanol is added to the mixture to discharge its red color and it is then filtered through Celite. The salts are washed with several portions of acetone. The filtrate is evaporated in vacuo. The residue is dissolved in 750 ml of diethyl ether and washed with sodium bicarbonate and brine solutions. After drying, the solvent is evaporated and the residue is distilled to yield the title compound; bp12 125 C. In a process analogous to Example B using appropriate starting materials the following compound is prepared:

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

Reference:
Patent; Warner-Lambert Company; US4988699; (1991); A;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 4891-38-7, name is Methyl Phenylpropiolate, 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 4891-38-7, category: esters-buliding-blocks

The reaction was carried out in a 10 ml Schlenk reaction tube. The reaction tube was evacuated and replaced with argon three times. 5 mol % (6.1 mg) of [Cp*RuCl2]2 (relative to substrate 1b) and 2 ml of solvent 1,2- were added. Dichloroethane, stirring 2min;Then 0.2 mmol (48.6 mg) of aziridine 1b and 1.0 mmol (160.2 mg) of methyl phenylpropiolate 2a are added and the reaction is heatedStir for 20 hours at 80C.After the reaction is completed, the solvent is removed by a rotary evaporator, and the solid is dissolved in dichloromethane and subjected to silica gel column chromatography using petroleum ether:The column was washed with an eluent of ethyl acetate = 10:1 – 5:1 (by volume) to give 46.8 mg of a white solid polysubstituted pyrrole compound 3b in an isolated yield of 58%.

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 Phenylpropiolate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Dalian Institute of Chemical Physics; Wan Boshun; Li Tengfei; Wu Fan; (17 pag.)CN107522645; (2017); A;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Electric Literature of 4897-84-1, A common heterocyclic compound, 4897-84-1, name is Methyl 4-bromobutanoate, molecular formula is C5H9BrO2, 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.

To a solution of the methyl ester (XIV, 1.8 g, 0.15 mmol) in DMF (50 mL), is added 4-bromo-butyric acid methyl ester (1 g, 0.87 mmol) and Cs2CO3 (800 mg, 0.48 mmol). The reaction is stirred at 22¡ã C. for 48 hours. 5 g SiO2 is added to the mixture and all solvents were evaporated in vacuo. The solid is purified by flash chromatography, eluting with MeOH/DCM (0-10percent) to provide 1.5 g (75percent), of a yellow solid. MS m/z 1357 (M +H2O).

The synthetic route of 4897-84-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Bushell, Simon; LaMarche, Matthew J.; Leeds, Jennifer; Whitehead, Lewis; US2009/156628; (2009); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Electric Literature of 884497-46-5, 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. 884497-46-5, name is Methyl 3-amino-5-fluorobenzoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Compound 14 (100 g, 591 mmol), compound 15 (107.68 g, 591 mmol) and dioxane (1000 ml) were added into a first reactor, then PPTS (60.82 g, 118.2 mmol) and MgSO4 (355.77 g, 2.96 mol) were added into the first reactor, then the first reactor was heated to reflux and stirred for 3 hours, cooled down to 50 C. NaBH4 (89.46 g, 2.36 mol) was added into the mixture and heated to 80 C., the first reactor was then stirred for 3 hours. After the reaction, the first reactor was cooled down to room temperature, methanol was added into the first reactor and white solid was filtered. The filtrate was concentrated and extracted by ethyl acetate, then washed with saturated NaHCO3 aqueous solution and sodium chloride aqueous solution. The organic phase was dehydrated with anhydrous sodium sulfate, filtered and concentrated to obtain crude product. The crude product was purified by column chromatography to give compound 16 (100 g, yield 53.3%). (0061)LC-MS (ESI) m/z: 318 (M+H)+.

The synthetic route of Methyl 3-amino-5-fluorobenzoate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Xu, Yong; Yohi, Peter W; Xu, Michael; Cruise, Douglas; (12 pag.)US9708319; (2017); B1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 34837-84-8, name is Methyl 2-(4-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 34837-84-8, category: esters-buliding-blocks

To a stirred solution of diisopropylamine (13.0 g) in tetrahydrofurane (160 mL)was added a solution of n-butyllithium in hexane (51 .4 mL; c= 2.5 M) at -78 ¡ãC.The solution was stirred at 0 ¡ãC for 15 minutes. The solution was cooled to -78¡ãC and a solution of methyl (4-fluorophenyl)acetate (18.0 g), dissolved intetrahydrofurane (40 mL) was added. The solution was stirred at -78 ¡ãC for 30 minutes. Methyl iodide (10.0 mL) was added at -78 ¡ãC, and the solution was allowed to warm up to 0 ¡ãC within 1 h. Water was added and the reaction mixture was extracted with ethyl acetate. The organic phase was dried (sodium sulfate) and the solvent was removed in vacuum. Silicagelchromatography gave 18.9 g of the title compound.1H-NMR (400MHz, DMSO-d6): 6 [ppm] = 1.34 (d, 3H), 3.55 (5, 3H), 3.79 (q, 1H),7.08 – 7.15 (m, 2H), 7.25 – 7.32 (m, 2H).

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

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; SCHULZE, Volker; LERCHEN, Hans-Georg; BIERER, Donald; WENGNER, Antje Margret; SIEMEISTER, Gerhard; LIENAU, Philip; KRENZ, Ursula; KOSEMUND, Dirk; STOeCKIGT, Detlef; BRUeNING, Michael; LUeCKING, Ulrich; TEREBESI, Ildiko; WO2014/198647; (2014); A2;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

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. 2475-80-1, name is Methyl 2-amino-5-methoxybenzoate, A new synthetic method of this compound is introduced below., Application In Synthesis of Methyl 2-amino-5-methoxybenzoate

The product is obtained by reacting 4.00 g (22 mmol) methyl 2-amino-5-methoxy-benzoate with 5 equivalents of ethylmagnesium bromide in dichloromethane at -78 C.?RT. Brown oil. Yield: 4.47 g (97%).

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; Boehringer Ingelheim International GmbH; US2006/189605; (2006); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Related Products of 41248-23-1, 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. 41248-23-1, name is Ethyl 1-hydroxycyclopentanecarboxylate, This compound has unique chemical properties. The synthetic route is as follows.

Example III-1′ 17.23 g (108.8 mmol) of ethyl 1-hydroxycyclopentanecarboxylate and 26.95 g (108.8 mmol) of 3-bromo-6-methylphenylacetyl chloride are combined, stirred at an oil bath temperature of 120 C. for 6 h and finally briefly heated to 140 C. and degassed on an oil pump.Yield: 39.73 g of an oil (99% of theory), log P (acidic) 4.52

The chemical industry reduces the impact on the environment during synthesis Ethyl 1-hydroxycyclopentanecarboxylate. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Bayer CropScience AG; US2011/306499; (2011); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Reference of 394-35-4, The chemical industry reduces the impact on the environment during synthesis 394-35-4, name is Methyl 2-fluorobenzoate, I believe this compound will play a more active role in future production and life.

3. 2-(2-((R)-sec-Butylamino)benzo[d]thiazol-6-yI)-3-(2-fluorophenyI)-3- oxopr op anenitrile[00170] To a solution of lithium bis(trimethylsilyl)amide (1.0 M in THF, 35.3 mL) in THF (60 mL) was added a solution of (R)-2-(2-(sec-butylamino)benzo[d]thiazol-6- yl)acetonitrile (3.74 g, 15.2 mmol) in THF (60 mL) at -780C over 40 min. The resulting solution was stirred at -780C for 10 min before a solution of methyl 2- fluorobenzoate (2.5 mL, 19.6 mmol) in THF (15 mL) was.added over 5 min. The mixture was stirred at -780C for 1 hr and then at rt for 3 hr before it was poured into ice-cold water (100 mL). After its pH value was adjusted to 9 with-6 N HCl, the mixture was extracted with AcOEt (3 x 60 mL). The combined extract was washed with brine and dried over anhydrous MgSO4. The solution was concentrated under EPO vacuum, and the residue was subjected to ISCO (2percent MeOH/CH2C12) to give a mixture (4.09 g) of the title compound and the starting material in a ratio of 1 : 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, Methyl 2-fluorobenzoate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; WO2007/16392; (2007); A2;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Related Products of 122-72-5, 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. 122-72-5 name is 3-Phenylpropyl Acetate, 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.

Acetyl chloride (2.64 g) was added into a mixture of aluminium chloride (3.74 g) and3-phenylpropyl acetate (5 g) in dichloromethane (DCM) (50 mL) at 0 C dropwise under N2. Then more aluminium chloride (3.74 g) was added. The resultant mixture was stirred at 0 C for 8 hours. The reaction mixture was poured into cold 2 M HC1 slowly, and then diluted with water. The obtained mixture was extracted with DCM for 3 times. The combined organic layers were dried over anhydrous Na2SC>4. After filtration, the filtrate was concentrated under reduced pressure, and the residue was purified by chromatography on silica gel (EtOAc : PE = 0-15 %) to afford 3-(4- acetylphenyl)propyl acetate (5.7 g) as a yellow oil. LH-NMR (400 MHz, CDC13) delta ppm 1.95-2.05 (m, 2H), 2.06 (s, 3H), 2.59 (s, 3H), 2.76 (t, J= 8.0 Hz, 2H), 4.09 (t, J= 6.4 Hz, 2H), 7.28 (d, J= 8.4 Hz, 2H), 7.90 (d, J= 8.0 Hz, 2H); MS(ES+) m/z 221 (MH+).

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

Reference:
Patent; GLAXO GROUP LIMITED; WANG, Yonghui; CAI, Wei; LIU, Qian; XIANG, Jia-Ning; WO2012/27965; (2012); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics