Diisobutylaluminumhydride → 4-Phenyl-but-3-enylamine

Temperature

0 °C

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.

1. temperatureto slowly warm to rt
2. customthen quenched
3. additionby carefully pouring the mixture onto 200 mL of 1:1 water/methanol at 0° C
4. customThe aluminum salts were removed by filtration
5. washwashed with methanol
6. customThe combined filtrate was collected
7. customthe volatile material was removed by a rotary evaporator

ORD record

ord-66725a1049364b39b741a7bdee9695b0

Source dataset

uspto-grants-2006_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07084154B2