Diisobutylaluminum hydride → (4-(1H-Benzo[d]imidazol-2-yl)phenyl)methanol

Participants

Reaction Steps

To a solution of methyl 4-(benzimidazol-2-yl)-benzoate (0.23 g, 0.9 mmol) in THF (10 mL) at 0° C. was added a solution of DIBAL-H (5.0 mL, 1.0 M in THF, 5.0 mmol). The reaction was allowed to warm to room temperature, stirred for 1 h and quenched with a saturated potassium sodium tartrate solution (20 mL). The biphasic mixture was stirred vigorously for 1 h, the phases separated and the organic layer dried (MgSO4), filtered, concentrated and purified by column chromatography on silica gel (7% MeOH/CH2Cl2) to give 4-(benzimidazol-2-yl)-benzyl alcohol (0.175 g, 87%). 1H NMR (CD4OD) δ3.30 (s, 1H (OH)), 4.69 (s, 2H), 7.26 (m, 2H), 7.53 (d, 2H, J=8.4 Hz), 7.60 (m, 2H), 8.07 (d, 2H, J=8.1 Hz).

Provenance & Evidence