Diisobutylaluminumhydride → (2-Methyl-indol-1-yl)-acetaldehyde

Participants

Reaction Conditions

Reaction Steps

A solution of (2-methyl-indol-1-yl)-acetic acid ethyl ester (400 mL, 1.97 mmol) in dimethoxyethane-dichloromethane (1:1, 30 mL) was cooled to −70° C. and treated with a solution of diisobutyl aluminum hydride in cyclohexane (3.9 mL, 1.0 M). The reaction was stirred at −70° C. for 4 h, quenched with an aqueous solution of hydrochloric acid (80 mL, 1 N) and extracted with ethyl acetate. The organic layers were combined, dried over sodium sulfate, filtered and concentrated, and the residue was purified to give (2-methyl-indol-1-yl)-acetaldehyde (234 mg, 75% yield). LCMS (m/z): 206.1 (M+1).

Provenance & Evidence