Imidazole → 5-(tert-Butyldimethylsilyloxy)-1H-indole

Participants

Reaction Steps

A solution of 5 g (37.55 mmol) of 5-hydroxy-indole, 6.13 g (39.4 mmol) of tert-butyldimethylsilyl chloride and 5.37 g (68.1 mmol) of imidazole in 50 ml DMF was stirred for 20 h at RT. The reaction mixture was taken up in ether, washed with 1N HCl and water and the ether solution was then concentrated under reduced pressure, to give 9.4 g (quant.) of clean 5-(tert-butyl-dimethyl-silanyloxy)-1H-indole.

Provenance & Evidence