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

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).

1. extractionextracted with diethyl ether (3×20 mL)
2. extractionThe combined extract
3. washwas washed with 0.5 N hydrochloric acid (2×10 mL), water and finally brine
4. dry with materialThe ethereal solution was dried over anhydrous MgSO4
5. filtrationfiltered
6. concentrationconcentrated in vacuo
7. customPurification of the product by flash column chromatography

ORD record

ord-88e58f0ee72043248cb0e097ce468c44

Source dataset

uspto-grants-2008_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07465825B2