Month: February 2021

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. 23786-14-3, name is Methyl 4-methoxyphenylacetate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Computed Properties of C10H12O3

NBS (9.06 g, 50.90 mmol) and AIBN (398 mg, 2.43 mmol) was added into a solution 2-(4-methoxyphenyl)acetate17(8.74 g, 48.50 mmol) in carbon tetrachloride (50 ml). The reaction was refluxed at 80Cfor 4h and quenched with water. Carbon tetrachloride was removed under vacuum. The reaction was extracted with ethyl acetate. The organic phase was washed with sodium thiosulfate (1M) and then saturated sodium chloride, dried over anhydrous sodium sulfate and concentrated to obtain the crude product18(12.43 g, 99% yield) as a white solid.1H NMR (400 MHz, CDCl3) delta 7.52-7.45 (m, 2H), 6.91-6.85 (m, 2H), 5.35 (s, 1H), 3.81 (s, 3H), 3.79 (s, 3H).

The synthetic route of 23786-14-3 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Li, Guangzhe; Dong, Huijuan; Ma, Yao; Shao, Kun; Li, Yueqing; Wu, Xiaodan; Wang, Shisheng; Shao; Zhao, Weijie; Bioorganic and Medicinal Chemistry Letters; vol. 29; 16; (2019); p. 2327 – 2331;,
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Some common heterocyclic compound, 176694-36-3, name is Methyl 4-fluoro-3-(trifluoromethyl)benzoate, molecular formula is C9H6F4O2, 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. HPLC of Formula: C9H6F4O2

3-Fluoroazetidine hydrochloride (1 10 mg, 0.99 mmol), /V,/V-diisopropylethylamine (0.34 ml_, 1.98 mmol) and methyl 4-fluoro-3-(trifluoromethyl)benzoate (200 mg, 0.90 mmol) were heated to 65 C in dimethyl sulfoxide (1 ml.) for 4 hours, by which time the starting material appeared to have been consumed by TLC. STEP 2: The reaction mixture was then concentrated under reduced pressure and the crude residue was dissolved in toluene (1 ml.) and ethanol (1 ml_). Hydrazine monohydrate (0.17 ml_, 3.60 mmol) was then added and the reaction mixture was heated at 65 C for 16 hours, by which time the starting material appeared to have been consumed by TLC. The reaction mixture was then concentrated under reduced pressure and the crude residue was recrystallised from cyclohexane and diethyl ether to give crude 4-(3- fluoroazetidin-1 -yl)-3-(trifluoromethyl)benzohydrazide (82 mg, 0.30 mmol, 33% yield) as a yellow solid that was used without further purification.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 176694-36-3, its application will become more common.

Reference:
Patent; UCL BUSINESS LTD; FISH, Paul, Vincent; MAHY, William; WILLIS, Nicky, John; WOODWARD, Hannah; ATKINSON, Benjamin, N; BAYLE, Elliott, D; SIPTHORP, James; JONES, Edith, Yvonne; ZHAO, Yuguang; VECCHIA, Luca; RUZA, Reinis, Reinholds; (208 pag.)WO2020/43866; (2020); A1;,
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Electric Literature of 3618-04-0, 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. 3618-04-0, name is trans-Ethyl 4-hydroxycyclohexanecarboxylate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

To a solution of 4-hydroxy-cyclohexanecarboxylic acid ethyl ester (10.32 g, 59.92 mmol) in dimethylformamide (50 mL) was added imidazole (8.16 g, 119.8 mmol), followed by tert-butyldimethylsilyl chloride (9.94 g, 65.9 mmol). The resulting mixture was stirred at room temperature for 16 hours. Diethyl ether was added (150 mL), and the mixture was washed with 1M [HC1] (150 mL). The aqueous layer was extracted with diethyl ether (150 mL). The combined organic layers were washed with 1M [HC1] (100 mL) and saturated sodium chloride solution (100 mL), dried over magnesium sulfate, filtered and concentrated to afford a clear oil. MS (CI) m/z 287 (M+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, trans-Ethyl 4-hydroxycyclohexanecarboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ABBOTT LABORATORIES; WO2004/26822; (2004); A2;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Synthetic Route of 73368-41-9, 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. 73368-41-9, name is Ethyl 4-amino-3-methoxybenzoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

After adding acetonitrile (170 mL) and N-chlorosuccinimide (13.4 g, 100 mmol) to ethyl 4-amino-3-methoxybenzoate (17.8 g, 91.2 mmol) in that order, the mixture was stirred at 60 C. for 2 hours. The mixture was returned to room temperature, and the solvent in the mixture was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (mixture of n-heptane and ethyl acetate: n-heptane/ethyl acetate=8/1 then 4/1) to obtain the title compound (15.8 g, 68.8 mmol). 1H-NMR (CDCl3) delta: 1.37 (t, J=6.8 Hz, 3H), 3.91 (s, 3H), 4.32 (q, J=6.8 Hz, 2H), 4.58 (br.s, 2H), 7.36 (d, J=1.8 Hz, 1H), 7.65 (d, J=1.8 Hz, 1H).

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 4-amino-3-methoxybenzoate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Eisai R & D Management Co., Ltd.; US2009/259049; (2009); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Application of 15568-85-1, 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 15568-85-1 as follows.

General procedure: 5-(Methoxymethylene)-2,2-dimethyl-1,3-dioxane-4,6-dione (0.5 g, 2.9 mmol) was added to a stirred solution of the 5-aminopyrazole 6 (2.9 mmol) in MeCN (10 mL). After stirring for 1 h, the solvent was removed in vacuo to complete the precipitation of the product.

According to the analysis of related databases, 15568-85-1, the application of this compound in the production field has become more and more popular.

Reference:
Article; Mackay, Martha; Nortcliffe, Andrew; McNab, Hamish; Hulme, Alison N.; Synthesis; vol. 47; 2; (2015); p. 242 – 248;,
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Reference of 87-24-1, 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. 87-24-1 name is Ethyl 2-methylbenzoate, 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.

Compound 1-1 (1.97g, 12mmol, 1eq), NBS (2.35g, 13.2mmol, 1eq), AIBN (98.4mg, 0.6mmol, 0.05 eq) was dissolved in 20mL of acetonitrile, the reaction was heated at reflux overnight, with TCL plate detection reaction, after completion of the reaction, the solvent under reduced pressure to give the crude product spin dry, and separated by a silica gel column, particle size of 200-300 mesh silica gel, eluent ratio of methylene chloride / petroleum ether = 1: 1, yields 56%.

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

Reference:
Patent; University of Jinan; Lin, Weiying; Ren, Mingguang; Deng, Beibei; (14 pag.)CN105884713; (2016); A;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Synthetic Route of 3618-04-0, The chemical industry reduces the impact on the environment during synthesis 3618-04-0, name is trans-Ethyl 4-hydroxycyclohexanecarboxylate, I believe this compound will play a more active role in future production and life.

tert-Butyldimethylchlorosilane (9.71 g, 64.45 mmol) was added portion wise to ethyl 4- hydroxycyclohexanecarboxylate (CAS no. 17159-80-7) (10 g, 58 mmol) and imidazole (7.9 g, 116 mmol) in DMF (58 mL) under nitrogen. The resulting solution was stirred at room temperature for 18 hours. The reaction mixture was diluted with diethyl ether (250 mL), and washed with saturated brine (500 mL). The organic layer was dried (MgSO4), filtered and evaporated to afford the product (16.3 g). This was used without any further purification.IH NMR (300 MHz, CDCl3) delta 0.02 – 0.07 (5H, m), 0.87 – 0.90 (9H, m), 0.92 (IH, s), 1.22 – 1.29 (3H, m), 1.30 – 1.54 (3H, m), 1.59 – 1.70 (2H, m), 1.87 – 2.04 (3H, m), 2.21 – 2.32 (IH, m), 3.70 – 3.89 (IH, m), 4.07 – 4.16 (2H, m).

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, trans-Ethyl 4-hydroxycyclohexanecarboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2009/24821; (2009); A2;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Electric Literature of 454-31-9,Some common heterocyclic compound, 454-31-9, name is Ethyl 2,2-difluoroacetate, molecular formula is C4H6F2O2, 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.

Step 2 Preparation of 4,4-difluoro-1-(3-fluoro-4-methoxyphenyl)-butane-1,3-dione Ethyl difluoroacetate (4.06 g, 32.7 mmol) was dissolved in methyl tert-butyl ether (50 mL). To the stirred solution was added 25 weight % sodium methoxide (7.07 g, 32.7 mmol) followed by 3′-fluoro-4′-methoxyacetophenone from Step 1 (5.0 g, 29.7 mmol). After stirring for 16 hours, 1N HCl (50 mL) was added. The organic layer was collected and washed with water (2*50 mL), dried over anhydrous MgSO4, filtered, and added to hexanes to precipitate a tan solid (7.0 g, 96%): mp 70-72 C.

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

Reference:
Patent; G. D. Searle & Co.; US6376528; (2002); B1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Related Products of 379228-57-6, These common heterocyclic compound, 379228-57-6, name is Methyl 2-amino-4,6-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.

A stirred solution of compound 16b (2.70 g, 14.42 mmol) in i-PrOH (50 mL) was cooled to 0C and added with NCS (2.02 g, 15.15 mmol) in portions, the resulting yellow suspension was stirred at 0C to 30C for 12 h while monitoring with LCMS (turned to clean gradually). The reaction mixture was concentrated in vacuum directly to give the crude product, which was purified by flash column chromatography on silica gel (Condition: 65-75%B (A: 0.05%TFA in water; B: MeOH) ; Flow rate: 40 ml/min)) to give compound 16c (1000 mg purity 87.20%, and 500 mg starting material) as a white solid. LCMS: R t = 0.905 min in 5-95AB_1.5 min_220&254 chromatography (MERCK RP18e 25-2mm), MS (ESI) m/z= 189.9 [M-32] +. 1H NMR (400MHz, DMSO-d 6) delta 7.04 (br s, 2H), 6.61 (dd, J=1.8, 11.8 Hz, 1H), 3.82 (s, 3H).

The synthetic route of 379228-57-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; DIZAL (JIANGSU) PHARMACEUTICAL CO., LTD; LI, Zhengtao; ZOU, Hao; ZHU, Wei; SHEN, Changmao; WANG, Rumin; LIU, Wengeng; CHEN, Xiang; TSUI, Honchung; YANG, Zhenfan; ZHANG, Xiaolin; (307 pag.)WO2019/149164; (2019); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Reference of 55666-43-8, 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 55666-43-8 as follows.

Preparation 12; 1,1-Dimethylethyl 3-[7-(5-{3-cyano-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-1,3,4,5-tetrahydro-2H-2-benzazepin-2-yl]propan-oate 2-[(1-Methylethyl)oxy]-5-[3-(2,3,4,5-tetrahydro-1H-2-benzazepin-7-yl)-1,2,4-oxadiazol-5-yl]benzonitrile hydrochloride (Example 3) (70 mg, 0.170 mmol) and caesium carbonate (167 mg, 0.511 mmol) were stirred in dry DMF (5 ml) and treated with 1,1-dimethylethyl 3-bromopropanoate (0.043 ml, 0.256 mmol) then stirred at 60 C. for 2 hours. Further quantities of 1,1-dimethylethyl 3-bromopropanoate (44 mul) were added and the reaction stirred at 60 C. for 3 hours. The reaction was left standing overnight. 1,1-Dimethylethyl 3-bromopropanoate (43 mul) was added and the reaction mixture stirred at 60 C. for 7 hours then left standing overnight. EtOAc (50 ml) was added and the reaction mixture washed with water (2¡Á50 ml), dried over anhydrous MgSO4 and evaporated to yield a clear, colourless oil (100 mg). The oil slowly solidified. Trituration with ether/hexane to yielded the title compound (70 mg) as a white solid. MS (ES) C29H34N4O4 requires 502. found 503.0 (M+H).

According to the analysis of related databases, 55666-43-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GLAXO GROUP LIMITED; US2010/174065; (2010); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics