Sodium borohydride → 5-Benzyloxy-2-[(4-benzyloxy-phenyl)-hydroxy-methyl]-phenol

Participants

Reaction Conditions

Reaction Steps

To a solution of (4-benzyloxy-2-hydroxy-phenyl)-(4-benzyloxy-phenyl)-methanone (T1) (1.6 g, 4 mmol) in 40 mL of THF:MeOH (1:1) was added sodium borohydride (0.160 g, 4 mmol) and solution stirred at 40° C. for 4 hours. After complete consumption of starting material (TLC) the solvents were evaporated, till about 5 mL remaining in the flask. The residue was carefully neutralized with 1 N H2SO4, till pH dropped to 6 and yellow solution turned colorless. This was extracted with 50 mL (4×EtOAc:water, 1:1). The organic layers were combined and dried over sodium sulfate and evaporated to give (1.12 g, 68%) of T2 as pinkish white solid. 1H NMR (400 MHz, DMSO-d6) δ, 9.42(s, 1H, OH-Ph), 7.30(m, 13H, Ar—H2′/6′, 2×C6H5), 6.89 (d, 2H, Ar—H3′/5′), 6.44 (dd, 1H, 2J=8.4 Hz, 3J=2.4 Hz, Ar—H5), 6.38 (d, 1H, J=2.4 Hz, Ar—H3), 5.51 (d, 1H, CH—OH), 5.04 (s, 2H, PhCH2), 4.99 (s, 2H, PhCH2).

Provenance & Evidence