Methanol → [4-isobutoxy-3-[(2-phenyl-1H-indol-1-yl)methyl]phenyl}methanol

Participants

Reaction Conditions

Reaction Steps

To a mixture of 4-isobutoxy-3-[(2-phenyl-1H-indol-1-yl)methyl]benzaldehyde (0.6 g, 1.56 mmol), methanol (3 mL) and tetrahydrofuran (6 mL) was added sodium borohydride (30 mg, 0.78 mmol) with stirring at 0° C., and the mixture was stirred at the same temperature for 1.5 hr. After completion of the reaction, the reaction mixture was diluted with ethyl acetate, and the mixture washed with 5% aqueous potassium hydrogensulfate solution and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=10/1-hexane/ethyl acetate=1/1) to give the title compound (0.60 g, yield 99%) as a colorless oil. 1H NMR (CDCl3) δ: 1.00 (6H, d, J=6.6 Hz), 1.37 (1H, t, J=6.0 Hz), 2.09 (1H, m), 3.79 (2H, d, J=6.6 Hz), 4.40 (2H, d, J=6.0 Hz), 5.36 (2H, s), 6.62 (1H, d, J=1.8 Hz), 6.68 (1H, s), 6.88 (1H, d, J=8.1 Hz), 7.10-7.18 (3H, m), 7.23 (1H, d, J=2.1, 8.4 Hz), 7.29-7.48 (5H, m), 7.68 (1H, m).

Provenance & Evidence