Ethyl Acetate → 1-(4-Amino-3'-chloro-biphenyl-3-yl)-ethanol

Participants

Reaction Steps

To a solution of 1-(4-amino-3′-chloro-biphenyl-3-yl)-ethanone (see example 35, 0.15 g, 0.61 mmol) in anhydrous methanol was added sodium borohydride (0.07 g, 1.03 mmol) at room temperature (rt) under nitrogen. After 15 minutes, the reaction mixture was treated with ice-water. Ethyl acetate (30 mL) was then added, the organic layer was separated, and aqueous layer was extracted with ethyl acetate (3×20 mL). The combined organic layers were washed with brine (10 mL) and dried over MgSO4. After removal of solvent, the residue obtained was crystallized from toluene to afford 1-(4-amino-3′-chloro-biphenyl-3-yl)-ethanol as a white solid (0.087 g, 58%): 1H-NMR (DMSO-d6) δ7.55 (t, 1H, J=1.4 Hz), 7.50 (d, 1H, J=7.8 Hz), 7.44 (d, 1H, J=2.1 Hz), 7.39 (t, 1H, J=8.2 Hz), 7.31-7.21 (m, 2H), 6.68 (d, 1H, J=8.1 Hz), 5.25 (s, 2H), 5.20 (m, 1H), 4.83 (m, 1H), 1.35 (d, 3H, J=8.8 Hz); MS (EI) m/z 247 (M+).

Provenance & Evidence