Month: July 2021

Electric Literature of 21905-56-6, 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. 21905-56-6, name is Methyl 2-phenoxybenzoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Step 2 2-Phenoxybenzylalcohol A 1.0 M solution of lithium aluminum hydride in THF (25 ml, 25 mmol) was added to a solution of crude 2-phenoxybenzoic acid methyl ester (5.23 g, 22.9 mmol) in THF. The reaction mixture was stirred for 2.5 hours at room temperature. Methanol (10 ml) was added carefully. THF (50 ml) was added. Magnesium sulphate was added. The solids were filtered off. The solvent was removed in vacuo. The crude product was purified by flash chromatography on silica (90 g), using ethyl acetate/heptane (1:1) as eluent, to give 4.08 g of 2-phenoxybenzylalcohol. 1H NMR (CDCl3) delta 4.70 (m, 2 H); 6.85 (d, 1 H); 6.97 (d, 2 H); 7.10 (m, 2 H); 7.25 (t, 1 H); 7.35 (t, 2 H); 7.45 (d, 1 H).

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

Reference:
Patent; Andersen, Knud Erik; Dorwald, Florencio Zaragoza; Peschke, Bernd; US2001/49385; (2001); A1;,
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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. 33993-24-7, name is Cyclopropanecarboxylic anhydride, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 33993-24-7

Step 1 : To a solution of methyl 2-isocyanoacetate (72.7 g, 729 mmol) and DBU (1 1 1 g, 729 mmol) in THF (1 L) was added a solution of cyclopropanecarboxylic anhydride (112 g, 729 mmol) in THF (100 mL) portionwise at 5C. The mixture was stirred at rt overnight, concentrated and purified by flash chromatography (PE/EtOAc = 5:1 ) to afford methyl 5-cyclopropyloxazole-4- carboxylate lnt-1 a-11. 1H-NMR (CDCI3, 300 MHz): delta 1.04-1.18 (m, 4H), 2.74-2.79 (m, 1 H), 3.91 (s, 3H), 7.60 (s, 1 H)

According to the analysis of related databases, 33993-24-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GILEAD SCIENCES, INC.; KINZEL, Olaf; KREMOSER, Claus; SCHMITT, Aaron C.; GEGE, Christian; (205 pag.)WO2016/96115; (2016); A1;,
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Application of 34846-90-7, A common heterocyclic compound, 34846-90-7, name is Methyl 3-methoxyacrylate, molecular formula is C5H8O3, 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.

(Step 4) Synthesis of methyl 3-(4-(2-chloroethyl)phenyl)isoxazole-4-carboxylate N-Hydroxy-4-(2-chloroethyl)benzenecarboxyimidoyl chloride (2.07 g, 9.48 mmol) was dissolved in dichloromethane (5 ml), methyl 3-methoxyacrylate (1.32 g, 11.37 mmol) was added, and triethylamine (1.92 g, 18.97 mmol) was slowly added dropwise. The mixture was stirred overnight at room temperature. Water was added, and the mixture was extracted with dichloromethane. The extract was washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the obtained crude product was purified by silica gel chromatography (hexane:ethyl acetate=5:1) to give the title compound (1.46 g, 58percent). MS(ESI) m/z 266 (M+H)+.

The synthetic route of 34846-90-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; AJINOMOTO CO. INC; US2006/194850; (2006); A1;,
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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 7778-83-8 as follows. Application In Synthesis of Propyl 3-Phenylacrylate

The substrate is used cinnamic acidPropyl ester (47.6mg, 0.2mmol) and (S) -1,1′- binaphthyl-2,2′-diyl hydrogen phosphate (73.1mg, 0.21mmol, 1.01Equiv.), Was addedAfter N- bromosuccinimide, 30h is reacted, and other experimental conditions were the same method as in Example 1, to obtain a colorless oily liquid 97.2mg, yield 70.7%.Two non enantiomers by high performance liquid chromatography )The chalcone (41.6mg, 0.2mmol) and (R / S) -1,1′- binaphthyl-2,2′-diyl hydrogen phosphate (73.1mg, 0.21mmol, 1.01Equiv.) Was dissolved in 2mLTHF ; and at room temperature, under argon atmosphere, was slowly every 2hWas added N- bromosuccinimide (0.1mmol, 0.5Equiv.) For a total of 4 times was added, N- bromosuccinimide was added, reaction was continued for 24h, the solvent was removed under reduced pressure, the residue by column chromatography gel (ethyl acetate: n-hexane; (1: 10, V / V, 100mL), (1: 5, V / V100mL), (1: 3, V / V, 200mL)), to give a colorless oily liquid121.7mg, yield 86%.The product form two diastereomers by high performance liquid.

According to the analysis of related databases, 7778-83-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Dalian Institute of Chemical Physics; Zhao, Zongbao; Suo, Heier; Liu, Wujun; (44 pag.)CN105524110; (2016); A;,
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Electric Literature of 25597-16-4, 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 25597-16-4 as follows.

Step 5: ethyl 6,8-(dimethyl-D6)-2-(trifluoromethyl)-2H-chromene-3-carboxylate The resulting product (2.02 g, 0.013 mol) from step 4, ethyl 4,4,4-trifluorocrotonate (4.30 g, 0.026 mol) and anhydrous potassium carbonate (1.76 g, 0.013 mol) were dissolved in DMF (70 mL), and then the system was stirred for 6 hrs at 80 C. At the end of reaction, the reaction system was cooled to room temperature, added with water and then extracted with ethyl acetate, and the organic phase was dried and evaporated in vacuum to obtain 2.35 g of the product (60.1%) by column chromatography. 1HNMR (400 MHz, d6-DMSO), delta ppm 7.84 (s, 1H), 7.13 (s, 1H), 7.09 (s, 1H), 5.94 (m, 1H), 4.25 (dd, 1H), 1.27 (t, 3H)

According to the analysis of related databases, 25597-16-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Guangzhou Institutes of Biomedicine and Health, Chinese Academy of Sciences; Zhang, Yanmei; Talley, John Jeffrey; Obukowicz, Mark G.; Tu, Zhengchao; Tortorella, Micky; Wang, Yican; Liu, Jianqi; Chen, Yan; Liu, Xiaorong; Lu, Xin; US2015/133538; (2015); A1;,
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Related Products of 52273-79-7, 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. 52273-79-7, name is Ethyl 2-(3-aminophenyl)acetate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

EXAMPLE 6 N-(3-Ethoxycarbonylmethylphenyl)-L-glutamine: Compound (6) Following the procedure described in (a) of Example 1, 11.14 g (0.03 mole) of N-carbobenzoxy-L-glutamic acid alpha-benzyl ester was reacted with 4.96 g (0.03 mole) of ethyl m-aminophenylacetate to give 12.95 g (81% yield) of an intermediate. The intermediate was dissolved in 500 ml of tetrahydrofuran, 200 ml of ethanol and 100 ml of water. To the solution was added 0.3 g of palladium black and the mixture was subjected to hydrogenation at atmospheric pressure to give 6.58 g (89% yield) of N-(3-ethoxycarbonylmethylphenyl)-L-glutamine, m.p. 175.5-176.2 C. [alpha]D25 =+26.4 (c=1 2 N HCl)

The synthetic route of Ethyl 2-(3-aminophenyl)acetate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Mitsubishi Chemical Industries Ltd.; Nippon Shinyaku Co., Ltd.; US4439448; (1984); A;,
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Some common heterocyclic compound, 5445-17-0, name is Methyl 2-bromopropanoate, molecular formula is C4H7BrO2, 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. Safety of Methyl 2-bromopropanoate

General procedure: To a solution of appropriate amount of 3-(arylimino)-2,3-dihydro-1H-isoindol-1-one 15 (0.75 mmol) in 10 cm3 dryacetone methyl 2-bromoalkanoate (1.12 mmol), 0.186 gpotassium iodide (1.12 mmol), and 0.207 g anhydrouspotassium carbonate (1.5 mmol) were added. The obtainedmixture was stirred at room temperature until the TLCshowed the absence of starting isoindolone 15(* 2-3 days). After that inorganic salts were filtered offand washed with 5 cm3 acetone. The filtrate was concentratedunder reduced pressure and the crude product waspurified by column chromatography (EtOAc/petroleumether 1:1) to afford the desired compound 16.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5445-17-0, its application will become more common.

Reference:
Article; Tkachuk, Volodymyr A.; Hordiyenko, Olga V.; Omelchenko, Irina V.; Medviediev, Volodomir V.; Arrault, Axelle; Monatshefte fur Chemie; vol. 149; 12; (2018); p. 2293 – 2309;,
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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. 19063-56-0, name is 7-Bromo-2H-chromen-2-one, A new synthetic method of this compound is introduced below., HPLC of Formula: C9H5BrO2

N-butyl-1,8-naphthalimide borate 11 (0.2 g, 0.53 mmol), 7-bromocoumarin(0.12 g, 0.53 mmol), Pd(PPh3)4 (0.024 g, 4 mol%) and 2Msodium carbonate solution (4 mL) were dissolved in THF (20 mL). Thereaction mixture was left for 8 h under nitrogen atmosphere at 70 C.After completion of the reaction, the reaction mixture was cooled toroom temperature and poured into water (50 mL), then extracted withdichloromethane (50 mLx 2). The organic layer was separated, washedwith saturated brine solution, dried over Na2SO4 and concentrated invacuum. The resulting residue was purified by column chromatographyon silica gel with hexane: ethyl acetate (8:2, v/v) as eluant. NC 4 wasobtained in 52.5% yield (0.11 g), m. p. 222 C. IR (KBr): numax/cm-11729 (nuCO), 1691 (nuCO). 1H NMR (400 MHz, CDCl3) delta 8.687-8.658 (m,2H, aromatic), 8.218 (d, 1H, J=8.8 Hz, aromatic), 7.836 (d, 1H,J=9.6 Hz, aromatic), 7.766-7.672 (m, 3H, aromatic), 7.503 (s, 1H,aromatic), 7.447 (d, J=8 Hz, 1H, aromatic), 6.546 (d, 1H, J=9.6 Hz),4.224 (t, 2H, J=7.6 Hz, CH2), 1.788-1.712 (m, 2H, CH2), 1.521-1.446(m, 2H, CH2), 0.996 (t, 3H, J=7.6 Hz, CH3)·13C (150 MHz, CDCl3) delta164.11, 163.88, 160.36, 154.01, 144.40, 142.87, 142.59, 131.77,131.41, 130.64, 129.63, 128.64, 128.10, 127.92, 127.35, 126.08,123.10, 122.66, 118.73, 118.20, 117.45, 40.34, 30.17, 20.37, 13.84.HRMS (m/z): [M+H] calculated for C25H20NO4: 398.1392; Found:398.1384

The synthetic route of 19063-56-0 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Reddy, T. Sheshashena; Hwang, Jiyoung; Choi, Myung?Seok; Dyes and Pigments; vol. 158; (2018); p. 412 – 419;,
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Adding a certain compound to certain chemical reactions, such as: 34846-90-7, name is Methyl 3-methoxyacrylate, 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 34846-90-7, HPLC of Formula: C5H8O3

A mixture of Intermediate-8C (1 equiv) and methyl 3-methoxyacrylate (3 equiv) was stirred at 90 °C for 6 h. The solvent was removed in vacuo and purification by silica gel chromatography (0-7percent methanol/dicloromethane) delivered the desired compound as a colorless solid (41percent). Intermediate-11: 1H NMR (400 MHz, CDC13) delta 10.46 (br s, 1H), 8.51 (d, 1H), 7.96 (d, 1H), 7.31 (s, 1H), 7.31-7.24 (m, 1H), 7.07-7.02 (m, 3H), 6.60 (d, 1H), 6.38 (d, 1H), 5.89 (s, 2H).

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; IRONWOOD PHARMACEUTICALS, INC.; KIM, Charles; NAKAI, Takashi; MOORE, Joel; PERL, Nicholas, Robert; IM, G-yoon, Jamie; BARDEN, Timothy, Claude; IYENGAR, Rajesh, R.; ZIMMER, Daniel, P.; FRETZEN, Angelika; RENHOWE, Paul, Allan; WO2013/101830; (2013); A1;,
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Adding a certain compound to certain chemical reactions, such as: 4630-80-2, name is Methyl cyclopentanecarboxylate, 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 4630-80-2, category: esters-buliding-blocks

General procedure: Into an oven-dried reaction vial flushed with N2 were taken esters 8 (0.60 mmol) and anhydrous toluene (3.0 mL). The reaction vial was cooled to -78C and LDA (2M in THF, 0.36 mL) was added dropwise with stirring. After 1h at -78C, sulfinylimine 7 (0.5 mmol) dissolved in anhydrous toluene (2.0 mL) was added dropwise. Stirring was continued for 2 h with the temperature gradual rising to room temperature, then the reaction was quenched with saturated H2O (3.0 mL). The organic layer was taken and the aqueous layer was extracted with EtOAc (2×20 mL). The combined organic layers were dried with anhydrous Na2SO4, filtered and the solvent was removed to give the crude product 9, which was purified by column chromatography (hexane/EtOAc, 4:1).

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

Reference:
Article; Dai, Yanling; Xie, Chen; Mei, Haibo; Han, Jianlin; Soloshonok, Vadim A.; Pan, Yi; Tetrahedron; vol. 71; 51; (2015); p. 9550 – 9556;,
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