Chemical synthesis method of 2- (2'-pyridyl) cyclopropanecarboxylic acid derivatives
A technology of chemical synthesis and cyclopropanecarboxylic acid, applied in the direction of organic chemistry, can solve the problems of cumbersome operation process, low yield, expensive catalyst, etc., and achieve the effect of high reaction yield and mild reaction conditions
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Embodiment 1
[0021] Synthesis of ethyl 3-(5-methyl-2'-pyridyl)acrylate:
[0022] 15.0 g of 5-methyl-2-pyridinecarboxaldehyde and 200 ml of dichloromethane (DCM) were added to a 500 ml four-necked flask, then 44.2 g of ethoxyformyl methylene triphenylphosphine were added, and the mixture was stirred uniformly in a greenhouse. TLC follow-up monitoring (ethyl acetate PE:petroleum ether EA=2:1) was used to determine the reaction endpoint. After the reaction, the reactant was concentrated, dissolved in water, extracted with methyl tert-butyl ether (MTBE), and the product obtained by extraction was passed through a column to remove impurities to obtain pale yellow 3-(5-methyl-2'-pyridine) base) ethyl acrylate, with a mass of 23.0 g and a yield of 97%.
[0023] Synthesis of ethyl 2-(5-methyl-2'-pyridyl)cyclopropanecarboxylate:
[0024] Under nitrogen protection, add 200 ml of dimethyl sulfoxide (DMSO) and 2.9 g of NaH into a 500 ml three-necked flask, add trimethyl sulfoxide iodide in batches...
Embodiment 2
[0028] Synthesis of ethyl 3-(6-methyl-2'-pyridyl)acrylate:
[0029] 15.0 g of 6-methyl-2-pyridinecarboxaldehyde and 200 ml of dichloromethane (DCM) were added to a 500 ml four-necked flask, then 44.2 g of ethoxyformyl methylene triphenylphosphine were added, and the mixture was stirred uniformly in a greenhouse. TLC follow-up monitoring (ethyl acetate PE:petroleum ether EA=2:1) was used to determine the reaction endpoint. After the reaction, the reactant was concentrated, dissolved in water, extracted with methyl tert-butyl ether (MTBE), and the extracted product was passed through a column to remove impurities to obtain pale yellow 3-(6-methyl-2'-pyridine) base) ethyl acrylate, with a mass of 22.4 g and a yield of 94.5%.
[0030] Synthesis of ethyl 2-(6-methyl-2'-pyridyl)cyclopropanecarboxylate:
[0031] Under nitrogen protection, add 200 ml of dimethyl sulfoxide (DMSO) and 2.9 g of NaH into a 500 ml three-necked flask, add trimethyl sulfoxide iodide in batches to the thr...
Embodiment 3
[0035] Synthesis of ethyl 3-(6-methoxy-2'-pyridyl)acrylate:
[0036] Add 17.0 g of 6-methoxy-2-pyridinecarboxaldehyde and 200 ml of dichloromethane (DCM) to a 500 ml four-necked flask, then add 44.2 g of ethoxyformyl methylene triphenylphosphine, and stir evenly in a greenhouse . TLC follow-up monitoring (ethyl acetate PE:petroleum ether EA=2:1) was used to determine the reaction endpoint. After the reaction, the reactant was concentrated, dissolved in water, extracted with methyl tert-butyl ether (MTBE), and the extracted product was passed through a column to remove impurities to obtain yellow 3-(6-methoxy-2'-pyridine) base) ethyl acrylate, with a mass of 23.5 g and a yield of 91.5%.
[0037] Synthesis of ethyl 2-(6-methoxy-2'-pyridyl)cyclopropanecarboxylate:
[0038] Under nitrogen protection, add 200 ml of dimethyl sulfoxide (DMSO) and 2.9 g of NaH into a 500 ml three-necked flask, add trimethyl sulfoxide iodide in batches to the three-necked flask, a total of 26.8 g,...
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