HCID 59243456, compound → HCID 20472015, compound

Participants

Reaction Steps

A slurry of (1-benzyl-1H-imidazol-2-yl)(diphenyl)methyl acetate (1-3, 13.1 g, 34.0 mmol, 1 equiv) and 10% palladium on carbon (6.03 g, 56.4 mmol, 1.66 equiv) in ethanol (250 mL) was stirred under hydrogen (balloon) for 24 h. The reaction mixture was filtered through a pad of celite and washed thoroughly with ethyl acetate. The combined filtrate was concentrated to dryness, and the residue was suspended in saturated aqueous sodium bicarbonate solution. The product was filtered, washed with water (2×100 mL) followed by a 1:1 mixture of ethyl ether and hexanes (2×50 mL) and air dried to yield 2-(diphenylmethyl)-1H-imidazole (1-4) as a white solid. 1H NMR (300 MHz, DMSO) δ 11.8 (br s, 1H), 7.29 (d, 6H, J=4.3 Hz), 7.21 (m, 4H), 7.03 (br s, 1H), 6.85 (br s, 1H), 5.51 (s, 2H), 1.84 (s, 3H). LRMS m/z (M+H) 235.0 found, 335.1 required.

Provenance & Evidence