Imidazole → 160701-58-6

Participants

Reaction Steps

To a solution of 3-hydroxyphenylacetic acid (1.5 g) in dimethylformamide (15 ml), 3.4 g of imidazole and 4.5 g of tert-butyldimethylchlorosilane was added, and the reaction solution was stirred overnight at room temperature. The reaction solution was diluted with water and extracted with ethyl acetate. The combined organic layers were washed with a saturated saline solution and then dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure to afford a crude product as a brown oil. To a solution of lithium aluminum hydride (748 mg) in tetrahydrofuran (10 ml), a solution of the crude product in tetrahydrofuran (5 ml) was added under ice-cooling, and the reaction solution was stirred at the same temperature for 1 hour. To the reaction solution was added sodium sulfate decahydrate, the mixture was stirred at the same temperature for further 1 hour and then Celite-filtered, and the filtrate was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate (98:2-50/50)) to afford the title compound as a yellow oil.

Provenance & Evidence