Imidazole → 4-(t-Butyldimethylsilyloxy)indole

Participants

Reaction Steps

To a suspension of 4-hydroxyindole (5.65 g, 42.4 mmol) in chloroform (200 mL) are added imidazole (4.33 g, 63.6 mmol) and tert-butylchlorodimethylsilane (7.03 g, 46.6 mmol), and the mixture is stirred at room temperature for 2.5 hours. The reaction mixture is washed with a mixture of a saturated brine and water (1:1, 100 mL), and the organic layer is dried over anhydrous potassium carbonate, filtered, and the filtrate is concentrated to about 50 mL under reduced pressure. The resultant is purified by silica gel column (300 g, ethyl acetate:hexane=1:5→1:1) to give the title compound as a white solid (3.90 g, yield: 37%), and the starting compound (2.62g, recovery rate: 46%).

Provenance & Evidence