Hydrochloric Acid → 5-(4-fluorophenyl)-2-hydroxymethyl-4-(4-methylthiophenyl)-1H-imidazole

Participants

Reaction Steps

A solution of compound from step 3 (350 mg, 1 mmol) and NaBH4 (75 mg, 2 eg.) in methanol (10 ml) was stirred for 1 hour at 25° C. The reaction was acidified with 2N HCl (4 ml), stirred for 2 hours and placed on a steam bath for 2 minutes. After cooling, the mixture was neutralized with aqueous NaHCO3 solution, extracted with methylene chloride, dried (MgSO4) and evaporated. The residue was chromatographed on silica gel, eluting with toluene/methanol (90/10). The crude product was recrystallized from ethyl acetate/hexane to give 240 mg (78%) of pure 5-(4-fluorophenyl)-2-hydroxymethyl-4-(4-methylthiophenyl)-1H-imidazole: m.p. 108°-110° C. Anal. Calc'd. for C17H15N20FS: C, 64.95; H, 4.81; N, 8.91; S, 10.20. Found: C, 64.69; H, 4.92; N, 8.79; S, 10.41.

Provenance & Evidence