Ammonium Chloride → [4-(2-Methylimidazol-1-yl)phenyl]methanol

To 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).

1. extractionthe whole extracted with ethyl acetate (100 ml×2)
2. washThe organic layer was washed with water (100 ml), brine (50 ml)
3. dry with materialdried over MgSO4, and solvent
4. customremoved under reduced pressure
5. washThe crude product was washed with an Et2O/ethyl acetate mixture (3:1, 15 ml)

ORD record

ord-bc71e60e4a684e24aa7197a8d701537d

Source dataset

uspto-grants-1998_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05753682