[H-].[Na+].[CH3:3][C:4]1[NH:5][C:6]2[CH:12]=[CH:11][CH:10]=[CH:9][C:7]=2[N:8]=1.[C:13]1([CH3:28])[CH:18]=[CH:17][CH:16]=[C:15]([O:19][C:20]2[CH:27]=[CH:26][C:23]([CH2:24]Br)=[CH:22][CH:21]=2)[CH:14]=1.O>CN(C)C=O>[CH3:3][C:4]1[N:8]([CH2:24][C:23]2[CH:22]=[CH:21][C:20]([O:19][C:15]3[CH:14]=[C:13]([CH3:28])[CH:18]=[CH:17][CH:16]=3)=[CH:27][CH:26]=2)[C:7]2[CH:9]=[CH:10][CH:11]=[CH:12][C:6]=2[N:5]=1To a suspension of sodium hydride (0.14 g, 3.6 mmole; 62% in oil) in anhydrous dimethylformamide (10 ml), 2-methylbenzimidazole (0.48 g, 3.6 mmole) was added while stirring, and stirring was continued at room temperature for 1 hour. The resultant mixture was cooled to 5°-10° C., and a solution of 4-(3-tolyloxy)benzyl bromide (1.00 g, 3.6 mmole) in anhydrous dimethylformamide (5 ml) was dropwise added thereto in 30 minutes, followed by stirring at room temperature overnight. After completion of the reaction, the reaction mixture was poured into water (100 ml) and extracted with toluene (30 ml) two times. The toluene layer was washed with water, dried over anhydrous sodium sulfate and distilled under reduced pressure to remove toluene. The residue was purified by silica gel column chromatography to give 2-methyl-1-[4-(3-tolyloxy)benzyl]benzimidazole (0.84 g) as colorless liquid. nD27.0 1.6112.
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