Anisole → HCID 22130792, compound

Participants

Reaction Steps

To a solution of 1-benzyloxymethyl-2-t-butyldimethyl-silyloxymethyl-5-(3-chlorophenylthio)imidazole (45) in nitromethane (108 ml) was added 14.7 g of (137 mmol) of anisole, and then, 18.1 g (136 mmol) of anhydrous aluminium chloride was gradually added at lower than 30° C. After completion of the addition, the mixture was stirred at room temperature for 15 minutes. The reaction mixture was cooled, and there were added water and a saturated aqueous sodium hydrogen carbonate solution to be alkaline. Ethyl acetate was added to the mixture, and the mixture was filtered on Hiflow Super Cell to separate. The organic layer was washed with water, dried over sodium sulfate, and the solvent was concentrated under reduced pressure. The residue was purified by silica gel chromatography (7% methanol-methylene chloride) to give 9.5 g of [5-(3-chlorophenylthio)-1H-imidazol-2-yl]methanol as oil (yield 87%).

Provenance & Evidence