Diisobutylaluminumhydride → 4-Phenyl-but-3-enylamine

Participants

Reaction Conditions

Reaction Steps

A suspension of 4-phenyl-but-3-enoic acid amide (5.0 g, 31 mmol) in 250 mL dichloromethane was cooled to 0° C. Diisobutylaluminum hydride (1 M in dichloromethane, 250 mL) was added and the resulting homogeneous mixture was allowed to slowly warm to rt. The reaction was stirred for 4 days then quenched by carefully pouring the mixture onto 200 mL of 1:1 water/methanol at 0° C. The aluminum salts were removed by filtration and washed with methanol. The combined filtrate was collected and the volatile material was removed by a rotary evaporator to give of 4-phenyl-but-3-enylamine (3.62 g, 79%) as a pale yellow oil.

Provenance & Evidence