Реакция #6810

Уравнение реакции

4-phenyl-but-3-enoic acid amide

Diisobutylaluminum hydride

→

4-phenyl-but-3-enylamine

Выход 79.3%

Растворители

dichloromethane

Условия реакции

Обработка

1. 1
   Температураto slowly warm to rt
2. 2
   Другоеthen quenched
3. 3
   workup.ADDITIONby carefully pouring the mixture onto 200 mL of 1:1 water/methanol at 0° C
4. 4
   ДругоеThe aluminum salts were removed by filtration
5. 5
   Промывкаwashed with methanol
6. 6
   ДругоеThe combined filtrate was collected
7. 7
   Другоеthe volatile material was removed by a rotary evaporator

Методика

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.

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