Tetrabutylammonium Fluoride → (1-Methyl-2-phenyl-1H-imidazol-4-yl)methanol
Reaction equation
[Si]([O:18][CH2:19][C:20]1[N:21]=[C:22]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[N:23]([CH3:25])[CH:24]=1)(C(C)(C)C)(C1C=CC=CC=1)C1C=CC=CC=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[CH3:25][N:23]1[CH:24]=[C:20]([CH2:19][OH:18])[N:21]=[C:22]1[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of 4-(((tert-butyldiphenylsilyl)oxy)methyl)-1-methyl-2-phenyl-1H-imidazole (1.25 g, 2.93 mmol) in dry THF (25 mL) was cooled to 0° C. and tetrabutylammonium fluoride (5.9 mL, 5.86 mmol, 1M in THF) was added dropwise. The reaction mixture was allowed to warm up to room temperature and further stirred for 3 h. The reaction mixture was quenched with brine and extracted with EtOAc. The organic layer was dried over anhydrous Na2SO4 and concentrated under reduced pressure. The crude product was purified by column chromatography (silica 60-120 mesh, eluant 2-4% MeOH in CH2Cl2) to get (1-methyl-2-phenyl-1H-imidazol-4-yl)methanol (0.26 mg, yield 47%) as a white solid. 1H NMR (400 MHz, DMSO-d6) δ 7.68-7.66 (m, 2H), 7.50-7.41 (m, 3H), 7.11 (s, 1H), 4.92 (br s, 1H), 4.37 (s, 2H), 3.71 (s, 3H). MS (ESI) m/z: Calculated for C11H12N2O: 188.09. found: 188.9 (M+H)+.