Methyl acetoacetate → HCID 15107319, compound

Participants

Reaction Conditions

Reaction Steps

At -10° C., 61.5 g of methyl acetoacetate was dripped into 16.5 g of sodium hydride in 350 ml of THF. The mixture was cooled to -60° C. and 344 ml of 1.6 molar n-butyllithium solution in hexane was added. After all had been added, the mixture was stirred for 30 minutes at -60° C., and then 69.5 g of 5-formyl-3-isopropylisoxazole in 50 ml of THF was quickly dripped in at -60° C. The mixture was stirred for 30 minutes and then 10 ml of methanol followed by 30 g of acetic acid was added. After 10 minutes, the mixture was poured onto 500 g of ice, heated to room temperature, and stirred for 1 hour. The aqueous phase was extracted three times with methylene chloride, brought--with cooling--to a pH of 4.5 with dilute hydrochloric acid, and extracted with methylene chloride. The extract was washed with 5% strength sodium bicarbonate solution and water, dried with sodium sulfate, and the solvent was stripped off in a rotary evaporator. The residue was crystallized by stirring with methyl tert-butyl ether, followed by suction filtration. There was obtained 15 g of pure product.

Provenance & Evidence