Methanol → HCID 54320756, compound

Participants

Reaction Steps

To a solution of 4-(2-phenylimidazol-1-yl)benzonitrile (3.2 g, 13 mmol) in dichloromethane (30 ml) and toluene (20 ml) cooled to -78° C. was added dropwise diisobutylaluminum hydride (13 ml, 13 mmol: 1.02M solution in toluene) under a nitrogen atmosphere and the whole stirred at this temperature for 1.5 h. Saturated aqueous NH4Cl solution (20 ml) was then added carefully to the reaction mixture, and the whole allowed to warm to room temperature. The resulting gelatinous mixture was filtered through a pad of celite, washing with ethyl acetate (200 ml). The filtrate was washed with 0.3N HCl solution (100 ml), water (200 ml) and brine (100 ml), and the organic layer dried over MgSO4. Removal of solvent under reduced pressure provided crude product (2.5 g) which was dissolved in methanol (30 ml) and cooled to 0° C. NaBH4 (0.3 g, 8 mmol) was added in portions and the reaction mixture stirred for 30 min. Saturated aqueous NH4Cl solution (30 ml) was added to the reaction mixture and the whole extracted with ethyl acetate (20 ml×3). The organic layer was washed with water (10 ml), brine (10 ml), dried over MgSO4 and solvent removed under reduced pressure. The resultant crude product was washed with ethyl acetate (35 ml) to give the title compound (0.81 g, 25%) as a white powder.

Provenance & Evidence