Benzophenone → HCID 2852467, compound

Participants

Reaction Conditions

Reaction Steps

A solution of n-butyllithium in hexanes (1.6 M, 45.0 mL, 72.0 mmol, 1.14 equiv) was added to a solution of 1-benzylimidazole (1-1, 10.0 g, 63.2 mmol, 1 equiv) in THF (200 mL) at −78° C. and the resulting mixture was stirred for 20 min. A solution of benzophenone (15.5 mL, 95.0 mmol, 1.50 equiv) in THF (30 mL) was added and the reaction mixture was stirred at −78° C. for 1 h, then warmed to 23° C. The mixture was partitioned between saturated ammonium chloride solution (200 mL) and ethyl acetate (400 mL), and the organic layer was separated, dried over magnesium sulfate and concentrated to give a yellow oil. The oil was suspended in saturated aqueous sodium carbonate solution and the resulting precipitate was filtered, washed with water (200 mL) then ethyl ether (2×100 mL) and air dried to afford (1-benzyl-1H-imidazol-2-yl)(diphenyl)methanol (1-2) as a white solid. 1H NMR (300 MHz, DMSO) δ 7.25 (m, 12H), 7.04 (m, 2H), 6.93 (s, 2H), 6.78 (s, 1H), 5.02 (s, 2H). LRMS m/z (M-OH) 323.1 found, 323.2 required.

Provenance & Evidence