Hydrochloric Acid → N-Tosylindole

Participants

Reaction Steps

To a solution of indole 81 (10 g, 85 mmol) in DMF (50 mL) at 0° C. was added NaH (60% dispersion in mineral oil 4 g) and tosylchloride (24 g, 128 mmol) portionwisely. And the reaction mixture was stirred at room temperature for 2 h. The resulting solution was acidified with 2.0 M HCl, and organic layer was extracted with Et2O. After evaporating the volatile material with reduced pressure, the residue was purified by silica column chromatography to obtain titled compound 82 (19 g, 84%).

Provenance & Evidence