Butyryl chloride → 5-Butyryl-2-indolinone

Participants

Reaction Conditions

Reaction Steps

To 15 g of aluminum chloride suspended in 30 ml of 1,2-dichloroethane in an ice bath was added 7.5 g of 2-oxindole and then 12 g of butyryl chloride. The resulting suspension was stirred at 50° C. overnight. The mixture was poured into ice water and extracted 3 times with ethyl acetate. The combined ethyl acetate layers were washed with brine, dried over sodium sulfate, and concentrated to dryness to give a brown solid. The solid was chromatographed on silica gel (50% ethyl acetate in hexane) to give 4.3 g (38%) of 5-butanoyl-2-oxindole as a yellow solid.

Provenance & Evidence