Triethylsilane → 4-(2-Butyl-benzofuran-3-ylmethyl)-phenol

Participants

Reaction Steps

At −10° C., to a stirred solution of 4-[(2-butyl-benzofuran-3-yl)-hydroxy-methyl]-phenol (2.78 g, 9.39 mmol) in CH3CN was added portionwise triethylsilane (two ×1.50 mL, 18.78 mmol total, @ 0.5 h interval). To the reaction was added BF3 Et2O (1.19 mL, 9.39 mmol) and the reaction was stirred for 10 min. The reaction was quenched with sat. aq. K2CO3 and extracted with CH2Cl2. The organic extracts were washed with brine (3×), dried (MgSO4) and concentrated. Purification on silica gel gave 2.35 g (89%) the title compound as a white solid, mp 67-70° C. (DMSO-d6) δ0.87 (t, 3 H), 1.31 (sextet, 2 H), 1.62 (quintet, 2 H), 2.78 (t, 2 H), 3.84 (s, 2 H), 6.64 (d, 2 H), 7.02 (d, 2 H), 7.09 (dt, 1 H), 7.16 (dt, 1 H), 7.31 (d, 1 H), 7.42 (d, 1 H), 9.16 (s, 1 H). IR (KBr) 3300, 2950, 1610, 1510 and 1450 cm−1. mass spectrum (EI) mz 280M +).

Provenance & Evidence