Acetyl chloride → N-(7-tert-butyl-3,3-dimethyl-2,3-dihydrobenzo[b]furan-5-yl)acetamide

Participants

Reaction Steps

To a solution of 5-amino-7-tert-butyl-3,3-dimethyl-2,3-dihydrobenzo[b]-furan (400 mg, 1.84 mmol) and dimethylaminopyridine (247 mg, 2.024 mmol) in CH2Cl2 (20 mL) is added at 24° C. acetyl chloride (130 μL, 1.84 mmol) in a single portion. The reaction is stirred for 1 h, and monitored by TLC (hexane:EtOAc, 9:1). The mixture is diluted with Et2O (5 mL), and a fine precipitate is filtered off. The filtrate is evaporated to an orange solid which is purified by preparative TLC (hexane:EtOAc, 9:1) to yield N-(7-tert-butyl-3,3-dimethyl-2,3-dihydrobenzo[b]furan-5-yl)acetamide as a white solid.

Provenance & Evidence