1-methyl-1H-1,3-benzodiazole-2-carbaldehyde → (1-methyl-1H-1,3-benzodiazol-2-yl)methanol

Reaction equation

[CH3:1][N:2]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[N:4]=[C:3]1[CH:11]=[O:12].[BH4-].[Na+]>C1COCC1.CO>[CH3:1][N:2]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[N:4]=[C:3]1[CH2:11][OH:12]

Participants

Procedure

To 432 mg of 1-methyl-1H-benzoimidazole-2-carbaldehyde (2.7 mmol, 1 eq) dissolved in a mixture of THF (10 mL) and methanol (10 mL) was added 340 mg of sodium borohydride (9.0 mmol, 3.33 eq) in several portions. After 12 h the reaction mixture was quenched with water and extracted with ethyl acetate. The organics were washed with brine, dried over sodium sulfate, filtered and concentrated in vacuo to give (1-methyl-1H-benzoimidazol-2-yl)-methanol in quantitative yield. 1H NMR (400 MHz, DMSO-d6) δ ppm 3.8 (s, 3 H) 4.7 (d, J=5.6 Hz, 2 H) 5.6 (t, J=5.7 Hz, 1 H) 7.2 (m, 1 H) 7.2 (m, 1 H) 7.5 (m, 1 H) 7.6 (m, 1 H).