Water → Ethyl 4-(5-chloro-2-pyridyl)-2,4-dioxobutanoate

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Reaction Steps

Dimethyl oxalate (5 g) was added to sodium methoxide (2.26 g) in ethanol (100 mL), and the mixture was stirred for 5 minutes. 1-(5-Chloro-2-pyridyl)ethanone (3.26 g) was added to the mixture, followed by stirring at room temperature for 45 minutes. Water was added to the reaction mixture, and the resultant mixture was washed with diethyl ether. The aqueous layer was acidified with aqueous 1N hydrochloric acid, and chloroform was added thereto to partition the mixture. The organic layer was dried over sodium sulfate anhydrate, followed by filtration. The solvent was removed under reduced pressure, to thereby give 4-(5-chloro-2-pyridyl)-2,4-dioxobutanoic acid ethyl ester as a solid (4.12 g, 77%).

Provenance & Evidence