Diethyl Ether → 4-(p-Chlorophenyl)-4-methyl-2-pentenal

Participants

Reaction Conditions

Reaction Steps

A solution of 4-(p-chlorophenyl)-3-fluoro-4-methyl-2-pentenenitrile, (Z)- (15.6 g, 69.7 mmol) in diethyl ether is treated dropwise with diisobutylaluminum hydride (83.6 mmol, 83.6 mL of a 1 M solution in hexane) over 90 minutes at −45° C. under nitrogen, stirred at −40° C. for 35 minutes, and diluted sequentially with water and 2 N hydrochloric acid at −10° C. The resultant aqueous mixture is stirred at room temperature for one hour and extracted with diethyl ether. The organic extracts are combined, washed sequentially with water, 2 N hydrochloric acid and water, dried over anhydrous sodium sulfate, and concentrated in vacuo to give the title product as a brown oil (15.34 g, 97% yield).

Provenance & Evidence