[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+].[Cl-].[NH4+]>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]To a 0° C. solution of 1-methyl-1H-benzimidazole-2-carbaldehyde (1.1 g, 6.8 mmol) in anhydrous methanol (50 mL) was added sodium borohydride (350 mg, 9.3 mmol). The reaction mixture was stirred at room temperature for 5 hours. Saturated ammonium chloride solution (20 mL) was added. Methanol was evaporated. The resultant mixture was extracted with EtOAc (3×50 mL) and CH2Cl2 (1×50 mL). The organic extracts were combined, dried over MgSO4, filtered, evaporated, and dried in vacuo. (1-methyl-1H-benzimidazol-2-yl)methanol was obtained (1.1 g, 99% yield). The product was used without further purification.
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