Acetyl chloride → 4-[(Trimethylsilyl)ethynyl]-1,2,3,6-tetrahydropyridine hydrochloride

Participants

Reaction Steps

tert-Butyl 4-[(trimethylsilyl)ethynyl]-3,6-dihydropyridine-1(2H)-carboxylate (2.75 g, 9.8 mmol) was stirred in methanol (10 mL) and acetyl chloride (2.1 mL, 29.2 mmol) was added dropwise. The temperature rose from 18° C. to 30° C. during the addition, and the mixture was kept at 40° C. until there was no more starting material by tlc. The mixture was cooled to room temperature, EtOAc (15 mL) was added and the solid filtered off to give an off-white solid (1.6 g).

Provenance & Evidence