Citric Acid → {4-[(2-phenyl-1H-indol-1-yl)methyl]phenyl}methanol

Participants

Reaction Steps

Methyl 4-[(2-phenyl-1H-indol-1-yl)methyl]benzoate (2.8 g, 8.20 mmol) was dissolved in anhydrous tetrahydrofuran (100 mL) and the mixture was ice-cooled. A solution (13.5 mL, 20.3 mmol) of 1.5 mol/L diisobutylaluminum hydride in toluene was added dropwise to the solution. This solution was stirred under ice-cooling for 4 hr, and aqueous citric acid solution was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed with aqueous sodium chloride solution, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography (ethyl acetate:hexane=1:4-1:2) to give the title compound (2.25 g, yield 88%) as a colorless oil.

Provenance & Evidence