Benzyl chloroformate → Benzyl [1-(benzyloxy)but-3-en-2-yl]carbamate

Participants

Reaction Steps

Benzyl carbonochloridate (4.7 g, 27.4 mmol) was added dropwise over a period of 30 minutes to a mixture of 1-(benzyloxy)but-3-en-2-amine hydrochloride (3.9 g, 18 mmol) and Hunig's base (10.0 mL, 54.8 mmol) in acetonitrile (100 mL) at 0° C. The reaction mixture was stirred at room temperature for 16 hours. The reaction mixture was diluted with water and extracted with ethyl acetate. The organic layer was dried over sodium sulfate, filtered, and concentrated under reduced pressure to afford the crude product residue. The crude product residue was purified by silica gel chromatography (ethyl acetate/petroleum ether) to afford benzyl [1-(benzyloxy)but-3-en-2-yl]carbamate. MS ESI calc'd. for C19H22NO3 [M+H]+ 312. found 312. 1H NMR (300 MHz, CD3OD) δ 7.34-7.25 (m, 10H), 5.87-5.79 (m, 1H), 5.25-5.08 (m, 4H), 4.51 (s, 2H), 4.38-4.36 (m, 1H), 3.54-3.44 (m, 2H).

Provenance & Evidence