[CH3:1][C:2]1[N:3]([C:7]2[CH:14]=[CH:13][C:10]([CH:11]=[O:12])=[CH:9][CH:8]=2)[CH:4]=[CH:5][N:6]=1.[BH4-].[Na+].[NH4+].[Cl-]>CO>[CH3:1][C:2]1[N:3]([C:7]2[CH:14]=[CH:13][C:10]([CH2:11][OH:12])=[CH:9][CH:8]=2)[CH:4]=[CH:5][N:6]=1To a stirred solution of the crude 4-(2-methylimidazol-1-yl)benzaldehyde (1.0 g) in methanol(15 ml) cooled to 0° C. was added NaBH4 (0.2 g, 5.2 mmol) in portions over 15 min and the whole stirred for 1 h. A saturated aqueous NH4Cl solution (50 ml) was added to the reaction mixture and the whole extracted with ethyl acetate (100 ml×2). The organic layer was washed with water (100 ml), brine (50 ml), dried over MgSO4, and solvent removed under reduced pressure. The crude product was washed with an Et2O/ethyl acetate mixture (3:1, 15 ml) to give the title compound (0.51 g, 50 %) as a white powder. 1H NMR (CDCl3) δ: 7.5 (d, 2H, J=8 Hz), 7.28 (d, 2H, J=8 Hz), 7.01 (d, 1H, J=1 Hz), 6.99 (d, 1H, J=1 Hz), 4.78 (s, 2H), 2.35 (s, 3H).
Wird geladen…
