Diisobutylaluminumhydride → HCID 22491013, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of ethyl (2E)-3-(4-ethyl-7-methoxy-2,2-dimethyl-2H-chromen-6-yl)-2-fluoro-but-2-enoate (Compound 68, 349 mg, 0.96 mmol) in THF (15 mL) under argon at 0° C. was added diisobutylaluminum hydride (1.0 M in hexanes, 2.9 mL, 2.9 mmol). The resulting mixture was stirred at −78° C. for 4 h. The reaction was quenched slowly with saturated NH4Cl, celite, and diluted with diethyl ether. The resulting mixture was stirred at 25° C. for 1 h. The product was filtered through a pad of celite. The solution was dried over Na2SO4 and concentrated in vacuo. The residue was purified by flash column chromatography (silica gel, 1:4 ethyl acetate/hexane) to yield the title compound as a yellow solid.

Provenance & Evidence