C[O:2][C:3]([C:5]1[CH:16]=[CH:15][C:8]2[N:9]([CH2:13][CH3:14])[C:10]([CH3:12])=[N:11][C:7]=2[CH:6]=1)=O.[H-].[Al+3].[Li+].[H-].[H-].[H-].S([O-])([O-])(=O)=O.[Na+].[Na+].CC(OC)(C)C>C1COCC1>[CH2:13]([N:9]1[C:8]2[CH:15]=[CH:16][C:5]([CH2:3][OH:2])=[CH:6][C:7]=2[N:11]=[C:10]1[CH3:12])[CH3:14]
To a solution of 450 mg (2.06 mmol) of the title D compound, 1-ethyl-2-methyl-1H-benzoimidazole-5-carboxylic acid methyl ester in 5 mL of THF is added dropwise 2.1 mL (2.1 mmol) of lithium aluminum hydride (LAH, 1.0M in THF). The mixture is stirred at RT for 90 min, then saturated aqueous sodium sulfate solution is carefully added dropwise until a thick precipitate formed. MTBE is added to the mixture and the insoluble aluminum salts are removed by filtration through Celite. The solvent is removed under reduced pressure to give (1-ethyl-2-methyl-1H-benzoimidazol-5-yl)-methanol as an oil: 1H-NMR (CDCl3) δ 7.63 (s, 1H), 7.28 (m, 2H), 4.77 (s, 2H), 4.16 (q, 2H), 3.74 (t, broad, 1H), 2.60 (s, 3H), 1.40 (t, 3H); [M+1]+=191.
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