Diisobutylaluminum hydride → 5,6-Diphenylpyridine-2-carbaldehyde

Participants

Reaction Steps

General Procedure L. To a solution of ethyl 5,6-diphenylpyridine-2-carboxylate (Compound 21, 145 mg, 0.48 mmol) in CH2Cl2 (5 ml) at −78° C. was added DIBAL-H (0.72 ml, 0.72 mmol, 1.0 M in Toluene) and the mixture was stirred between −78° C. and −60° C. for 1 hour under argon. The reaction was quenched with aq, NH4Cl, diethyl ether and 400 mg Celite were added, and the mixture was stirred at room temperature 30 min. The solid was filtered off and rinsed with ether, and the combined filtrate was concentrated in vacuo, and the residue was purified by column chromatography (silica gel, 15% ethyl acetate in hexane) to produce the title compound.

Provenance & Evidence