Benzyl chloroformate → Benzyl 3-acetyl-1H-indole-1-carboxylate

Participants

Reaction Steps

To a stirred slurry of sodium hydride (3.77 g, 50% in oil, 7.86 mmol, extracted with hexanes) in THF (30 ml) at 0° C. under nitrogen was added dropwise 3-acetyl indole (10.0 g, 62.9 mmol) in THF (15 ml). After warming to room temperature and stirring one hour, the mixture was cooled to 0° C. and benzyl chloroformate (8.97 ml, 62.9 mmol) was added dropwise. The reaction was allowed to warm to room temperature and stir overnight. The excess sodium hydride was destroyed at 0° C. with 40 ml H2O. The mixture was then extracted three times with CHCl3 (total volume 120 ml), dried with MgSO4, filtered and evaporated to an off-white solid. Recrystallization from hexanes afforded 15.85 g (86%) of product: mp 112°-113°; Anal. Calcd for C18H15NO3 : C, 73.79; H, 5.16; N, 4.78. Found: C, 73.86; H, 5.29; N, 4.95.

Provenance & Evidence