Sodium Sulfate → 2-Amino-4-phenyl-3-butenenitrile

Participants

Reaction Conditions

Reaction Steps

10 millimoles (1.29 g) of cinnamonitrile are dissolved in 150 ml of anhydrous toluene at -70° C., under an argon atmosphere. 15 millimoles of a toluenic solution 1.5 M of diisobutylaluminum hydride (10 ml) are added, dropwise, at -70° C. The stirring is maintained at this temperature for 30 minutes, then 2 ml of trimethylsilyl cyanide are added at -40° C. The stirring is then maintained at -40° C. for 2 hours. The reaction mixture is then hydrolyzed at -20° C. with 10 ml methanol and with pasty sodium sulfate. The so-obtained product is purified by liquid chromatography on silica, in eluting with ethyl acetate/petroleum ether 1/1. There are obtained 0.515 g of purified 2-amino-4-phenyl-3-butene-nitrile; yield 33%.

Provenance & Evidence