Diisobutylaluminum hydride → HCID 53242308, compound

Participants

Reaction Steps

To a solution of ethyl 3-(4-cyanophenyl)propiolate (2.2 g, 11.04 mmol, 1.00 equiv) in dichloromethane (10 mL) maintained under nitrogen at −65° C. was added a 25% DIBAL (22 mL, 2.00 equiv) solution in toluene dropwise with stirring. The resulting solution was stirred at −65° C. for 2 h and then quenched by the addition of 5 mL of saturated sodium potassium tartrate solution. The solid material was removed by filtration. The filtrate was extracted with 3×30 mL of dichloromethane. The combined organic layers was dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was purified on a silica gel column eluted with 0-10% of methanol in dichloromethane to give 627 mg (37%) of 4-(3-oxoprop-1-ynyl)benzonitrile as a white solid.

Provenance & Evidence