Tag: M.W=200-300

Synthetic Route of 3044-06-2,Some common heterocyclic compound, 3044-06-2, name is Diethyl 2-(1-ethoxyethylidene)malonate, molecular formula is C11H18O5, 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 mixture of l-ethyl-lH-pyrazol-5-amine (16 gm, 0.144 moles) (example 2) and 2-(l-ethoxy-ethylidene)-malonic acid diethyl ester (29 gm, 0.12 moles) (example 3) was stirred at 1200C for about 2 hrs. When the reaction was complete on TLC, crude reaction mixture was concentrated in vacuo to remove ethanol, which was formed as byproduct. Crude residue was taken in phosphorous oxychloride (50 ml) and heated at 115 C for about 12-13 hrs. The reaction mixture was poured into ice-cooled water with continuous stirring. Solid which precipitated out was filtered and dried under vacuum to afford title compound as creamy white solid.Yield: 12 gm (57.17%) m/z: (M++l) 268.28

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Diethyl 2-(1-ethoxyethylidene)malonate, its application will become more common.

Reference:
Patent; RANBAXY LABORATORIES LIMITED; RUDRA, Sonali; GUPTA, Nidhi; CHANDRAKANT, Kakade, Ganesh; JAIN, Tarun; VOLETI, Sreedhara, Rao; RAY, Abhijit; DASTIDAR, Sunanda G.; VIJAYKRISHNAN, Lalitha; WO2010/46791; (2010); A1;,
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Related Products of 1459-96-7,Some common heterocyclic compound, 1459-96-7, name is Dimethyl bicyclo[2.2.2]octane-1,4-dicarboxylate, molecular formula is C12H18O4, 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.

At atmospheric conditions, 0.25g of the Ru-TRIPHOS catalyst ruthenium 1 ,1 ,1 -tris(diphenylphosphinomethyl)ethane, 25 mg of p-toluenesulfonic acid, 2.5g of dimethyl bicyclo[2.2.2]octane-1 ,4-dicarboxylate and 50 imL of p-xylene were added to a 100 imL autoclave reactor. The reactor was then purged three times by pressurizing with nitrogen to 200 psig, then venting the pressure to atmospheric each time. The reactor was then purged three times by pressurizing with hydrogen to approximately 300 psig, then venting the pressure to atmospheric each time. Agitation at 800 rpm was then commenced, and hydrogen was then added to bring the pressure to 1600 psig. The temperature was then increased to 200 C while allowing pressure to rise. After the temperature reaches 200 C, the hydrogen pressure was increased to 2000 psig. These conditions (200 C and 2000 psig) were held for 24 hours of reaction. After 24 hours of reaction, the agitation was stopped, and the heat turned off to let the autoclave start cooling. After cooling to room temperature, pressure was released, and the contents were purged with nitrogen gas and vented. The solution was finally discharged from the autoclave and analyzed by GC-MS and 1H NMR. The conversion of dimethyl bicyclo[2.2.2]octane-1 ,4-dicarboxylate is 30% and the only product methyl 4-(hydroxymethyl)bicyclo[2.2.2]octane-1 -carboxylate (100% selectivity).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Dimethyl bicyclo[2.2.2]octane-1,4-dicarboxylate, its application will become more common.

Reference:
Patent; EASTMAN CHEMICAL COMPANY; HU, Yue, Rachel; HEMBRE, Robert, Thomas; TUSTIN, Gerald, Charles; LIU, Zhufang; ADAMS, Steven, J.; CLARKSON, Jasper, Randle; (59 pag.)WO2019/75004; (2019); A1;,
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Electric Literature of 88709-17-5, The chemical industry reduces the impact on the environment during synthesis 88709-17-5, name is Ethyl 2-ethoxy-4-methylbenzoate, I believe this compound will play a more active role in future production and life.

Under an atmosphere of nitrogen, n-butyllithium (50 ml, 15% w/w solution in hexane) was added to a solution of diisopropylamine (7.25 g) in tetrahydrofuran (90 ml) at -30 C. The mixture was stirred at -30 C. for 30 minutes, cooled to -75 C., and 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone (DMPU, 30 ml), was added slowly. A solution of ethyl 2-ethoxy-4-methylbenzoate (10 g) in tetrahydrofuran (10 ml) was then added at -75 C. and the mixture was stirred for two hours. Carbon dioxide gas was then purged into the reaction mixture at -75 C. till complete decolorization. The reaction mixture was then brought to room temperature, diluted with water (100 ml), and extracted with dichloromethane (100 ml). The aqueous layer was acidified with 10% aqueous sulphuric acid to pH 1.95 and extracted with toluene. The combined toluene layer was washed with water and concentrated in vacuo. Crystallisation with ethyl acetate/petroleum ether afforded (3-ethoxy-4-ethoxycarbonyl)-phenyl acetic acid 7.2 g (59.5%).

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-ethoxy-4-methylbenzoate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Banbaxy Laboratories Limited; US6686497; (2004); B1;,
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Related Products of 40876-98-0, 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 40876-98-0 as follows.

5-Hydroxy-1-methyl-1H-pyrazole-3-carboxylic acid ethyl ester; [Show Image] (1) To a solution of diethyl oxalacetate sodium salt (30.0 g) in toluene (200 ml), acetic acid (200 ml) and methylhydrazine (15 ml) were added and stirred at 100C for 8.5 hours. The reaction mixture was concentrated, and the resulting residue was diluted with saturated aqueous sodium chloride and extracted with AcOEt. The resulting organic layer was dried over MgSO4, filtered and evaporated under reduced pressure to remove the solvent. The resulting solid was washed with Et2O/hexan (Et2O/hexane = 2/1) and dried to give the titled compound (18.8 g, brown powder). 1H NMR (600 MHz, DMSO-D6) delta ppm: 1.25 (t, J=7.1 Hz, 3 H), 3.59 (s, 3 H), 4.16-4.25 (m, 2 H), 5.77 (s, 1 H)

According to the analysis of related databases, 40876-98-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; TAISHO PHARMACEUTICAL CO., LTD; EP1988081; (2008); A1;,
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Some common heterocyclic compound, 109232-37-3, name is Isobutyl 5-chloro-2,2-dimethylvalerate, molecular formula is C11H21ClO2, 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. category: esters-buliding-blocks

Compound 1-1 (4-chloro-2,5-dimethylphenol) (780 mg, 5.0 mmol), 5-chloro-2,2-dimethylvaleric acid isobutyl ester (1144 mg, 5.2 mmol), TBAI (36.9mg, 0.1mmol), potassium carbonate (1380mg, 10.0mmol) was dissolved in DMF (30mL), and stirred at 90 C overnight. TLC monitors the tendency of discontinuous conversion. The reaction solution is poured into water and the layers are separated. After the aqueous phase is extracted with ethyl acetate, the organic phases are combined, dried over anhydrous sodium sulfate, filtered and the filtrate is concentrated. Compound 1-2 (1.5 g) was isolated by analysis and the yield was 88%.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 109232-37-3, its application will become more common.

Reference:
Patent; Beijing Hou Shenyaode Science And Technology Co., Ltd.; Jiao Ning; Yu Siwang; Song Song; Liu Yameng; Yang Simin; (60 pag.)CN110857268; (2020); 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. 29823-21-0, name is Ethyl 8-Bromooctanoate, A new synthetic method of this compound is introduced below., Recommanded Product: 29823-21-0

a) 2-(4-Methoxyphenyl)-4,5-diphenylimidazole (10 g) (J. Org. Chem., 1964, 29, 1926-30) was reacted with sodium hydride (1.7 g) and ethyl 8-bromooctanoate (9.6 g) in a method similar to Example 12. Chromatography on silica gel eluted with chloroform gave 1-(7-ethoxy-carbonylheptyl)2-(4-methoxyphenyl)-4,5-diphenylimidazole (12.9 g, 85%) as an oil.

The synthetic route of 29823-21-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SmithKline Beecham Corporation; The Johns Hopkins University; US5648373; (1997); A;,
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Synthetic Route of 457097-93-7,Some common heterocyclic compound, 457097-93-7, name is Methyl 4-amino-3-(trifluoromethoxy)benzoate, molecular formula is C9H8F3NO3, 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.

c) 4-Benzyloxycarbonylamino-3-trifluoromethoxy-benzoic acid methyl ester To a solution of 4-amino-3-trifluoromethoxy-benzoic acid methyl ester (4.9 g, 20.8 mmol) and NaHCO3 (5.24 g, 62.4 mmol) in dioxane-water 5:1 (90 mL) is added at 0-5 C. benzyl chloroformate (4.4 mL, 31.3 mmol). After addition the reaction mixture is stirred at 25 C. for 16 h. The reaction mixture is diluted with CH2Cl2 and washed with water, dried over MgSO4 and evaporated. The title compound is obtained after purification by flash-chromatography on silica gel (hexane-EtOAc 30:1 to 10:1) as a colorless oil: TLC (hexane-EtOAc 4:1) Rf=0.52; ESIMS [M-H]-=368.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Methyl 4-amino-3-(trifluoromethoxy)benzoate, its application will become more common.

Reference:
Patent; Briard, Emmanuelle; Lueoend, Rainer Martin; Machauer, Rainer; Moebitz, Henrik; Rogel, Olivier; Rondeau, Jean-Michel; Rueeger, Heinrich; Tintelnot-Blomley, Marina; Veenstra, Siem Jacob; US2009/54427; (2009); A1;,
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Some common heterocyclic compound, 150529-73-0, name is Methyl 2-(3-bromophenyl)acetate, molecular formula is C9H9BrO2, 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. name: Methyl 2-(3-bromophenyl)acetate

INTERMEDIATE 72-(3-BromophenyD-2-methylpropionic acid methyl esterA solution of Intermediate 6 (15.85 g, 69.2 mmol) in THF (50 mL) was added as a steady stream over about 5 minutes to a suspension of sodium hydride (60% dispersion in mineral oil, 8.32 g, 208 mmol) in THF (100 mL) under nitrogen in an ice-water bath whilst maintaining the internal temperature between 1O0C and 200C. After the addition was complete, the mixture was stirred at r.t. for 1 h. The mixture was cooled again in an ice-water bath, and a solution of methyl iodide (10.6 mL, 24.6 g, 173 mmol) in THF (100 mL) was added slowly so as to maintain the temperature of the reaction at <25C. After the addition was complete the mixture was stirred for a further 15 minutes with the ice- water bath, and then for 18 h. The mixture was poured slowly (over a period of about 2 minutes) onto a mixture of ice (approximately 100 g) and saturated ammonium chloride solution (100 mL). The resulting mixture was evaporated and extracted with DCM (2 x 50 mL). The combined organic phases were dried (MgSO4), the solvent removed in vacuo and purified by column chromatography (SiO2, 10-100% EtOAc in heptane) to give the title compound (17.3 g) as a pale straw-coloured oil. deltaH (CDCl3) 7.48 (t, IH), 7.38 (m, IH), 7.23-7.29 (m, IH), 7.19 (t, IH), 3.66 (s, 3H), 1.56 (s, 6H). These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 150529-73-0, its application will become more common. Reference:
Patent; UCB PHARMA S.A.; BUeRLI, Roland; HAUGHAN, Alan, Findlay; MACK, Stephen, Robert; PERRY, Benjamin, Garfield; RAPHY, Gilles; SAVILLE-STONES, Elizabeth, Anne; WO2010/52448; (2010); A2;,
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Adding a certain compound to certain chemical reactions, such as: 1186-73-8, name is Trimethyl methanetricarboxylate, 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 1186-73-8, Recommanded Product: Trimethyl methanetricarboxylate

Step 9: Methyl 10-chloro-l-(2,4-dimethoxybenzyl)-4-hydroxy-2-oxo-2,5,6,8-tetrahydro- lH-benzo[6,7]oxocino[5,4-b]pyridine-3-carboxylate 9-Chloro-N-(2,4-dimethoxybenzyl)-4,5-dihydro-lH-benzo[c]oxocin-6(3H)-imine (ca. 0.3 g, 0.8 mmol) and trimethyl methanetricarboxylate (0.35 g, 1.8 mmol) were mixed in Ph20 (5 mL). The stirred mixture was placed onto a pre-heated heat block at 230 C and heated for 10 min after initial bubbling of MeOH was observed (occurs at approx. 160 C internal reaction temperature). The reaction mixture was cooled to room temperature, loaded directly on a silica column, eluted first with hexanes to separate Ph20 and then EtOAc/hexanes gradient (0-50%) to yield the title compound (41 mg, 11% over 2 steps) as a yellow foam. LC-MS: 484.1 [M-H]+, RT 1.45 min.

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

Reference:
Patent; PTC THERAPEUTICS, INC.; GERASYUTO, Aleksey, Igorevich; ARNOLD, Michael, A.; CHEN, Guangming; KARP, Gary, Mitchell; QI, Hongyan; TURPOFF, Anthony, A.; WANG, Jiashi; WOLL, Matthew, G.; ZHANG, Nanjing; ZHANG, Xiaoyan; BRANSTROM, Arthur, A.; NARASIMHAN, Jana; DUMBLE, Melissa, L.; HEDRICK, Jean; WEETALL, Marla, L.; (229 pag.)WO2016/25932; (2016); A1;,
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Some common heterocyclic compound, 609-12-1, name is Ethyl 2-bromo-3-methylbutanoate, molecular formula is C7H13BrO2, 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. name: Ethyl 2-bromo-3-methylbutanoate

4-fluoro-3-nitrophenol (500 mg, 3.18 mmol) was dissolved in DMF (6.365 mL) at room temperature. Cesium Carbonate (1244 mg, 3.82 mmol) was added followed by ethyl 2-bromo-3-methylbutanoate (0.574 mL, 3.50 mmol). The mixture was stirred at 60 C. Reaction left at 60 C overnight. Reaction was then diluted with water and a precipitate formed. The solid was filtered off and dried on high vacuum overnight to yield 83A (tan solid, 615 mg, 2.156 mmol, 67.7 % yield), yield). LC-MS Anal. Calc’d for Ci3Hi6FN05 285.10, Tr = 1.04 min (Method A) (Note: product does not ionize well). NMR (400 MHz, MeOH-d4) delta: 7.60 (dd, J=6.0, 3.3 Hz, 1H), 7.53 (dd, J=10.9, 9.3 Hz, 1H), 7.38 (s, 1H), 4.84 (d, J=4.8 Hz, 1H), 4.16 (dd, J=7.1, 2.8 Hz, 2H), 2.20-2.30 (m, 1H), 1.15-1.20 (m, 3H), 1.01 (dd, J=6.8, 4.6 Hz, 6H) 83B.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 609-12-1, its application will become more common.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; BALOG, James Aaron; CHERNEY, Emily Charlotte; MARKWALDER, Jay A.; SHAN, Weifang; WILLIAMS, David K.; (203 pag.)WO2016/210414; (2016); A1;,
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