Diisobutylaluminum hydride → 3-(1-(3-Phenoxyphenyl)-2-oxabicyclo[2.2.2]octan-4-yl)propan-1-ol

Participants

Reaction Conditions

Reaction Steps

To a solution of 3-(1-(3-phenoxyphenyl)-2-oxabicyclo[2.2.2]octan-4-yl)propanal (40 mg, 0.119 mmol) in DCM (1 mL) at −78° C. under N2 was added 1M DIBAL-H in DCM (0.178 ml, 0.178 mmol). The reaction mixture was stirred at −78° C. for 2 h and then added CELITE® (250 mg). The reaction was quenched with sat′d aqueous NH4Cl (0.5 mL) at −78° C. and then stirred at rt for 30 min. MgSO4 (200 mg) was added and the mixture was stirred at rt for 1 h. The mixture was filtered. The solid was washed with DCM. The combined filtrates were concentrated in vacuo to afford the title compound (40 mg, 99% yield) as an oil. LCMS, [M+NH4]+=356.2.

Provenance & Evidence