Hydrochloric Acid → 4′-(1H-Indol-1-yl)[1,1′-biphenyl]-4-methanol

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Reaction Steps

Sodium borohydride (783 mg, 20.6 mmol) was added portion-wise to a stirred solution of aldehyde (prepared in example 4) (3.06 g, 10.3 mmol) in a mixture of anhydrous THF and ethanol (1:1; 100 mL) at room temperature. The reaction mixture was stirred for 10 minutes at room temperature (TLC control), poured into water (50 mL) and acidified to pH 4 with 2N hydrochloric acid, and then extracted with diethyl ether (3×20 mL). The combined extract was washed with 0.5 N hydrochloric acid (2×10 mL), water and finally brine. The ethereal solution was dried over anhydrous MgSO4, filtered and concentrated in vacuo. Purification of the product by flash column chromatography, using 30% ethyl acetate/hexane as eluent, afforded the title compound has a white solid (2.80 g, 91%); 1H NMR (CDCl3, 300 MHz) δ 7.55-7.78 (7H, m, Ar-H), 7.52 (2H, d, J=8 Hz, Ar-H), 7.41 (1H, d, J=3.5 Hz, Ar-H), 7.22 (3H, m, Ar-H), 6.72 (1H, d, J=3.5 Hz, Ar-H), 4.79 (2H, d, J=5.5 Hz, CH2O).

Provenance & Evidence