Hydrochloric Acid → 4-(1H-Indol-3-YL)cyclohexanone

Participants

Reaction Steps

To a 23° C. solution of 8.66 g (33.7 mmol) 3-(1,4-dioxa-spiro[4.5]dec-8-yl)-1H-indole and 200 mL THF was added 200 mL of 1N HCl. After stirring for 12 h, the organics were evaporated and the resulting slurry was extracted with 2×150 mL EtOAc. The combined organics were washed with 2×100 mL of 1N NaOH, dried over MgSO4, filtered and evaporated to an off-white solid. Flash chromatography on silica gel, eluting with hexanes/EtOAc (1/1) gave 5.89 g (27.6 mmol, an 82% yield) of the title compound as a white solid. mp 123-125° C.; MS (ES) m/z (relative intensity): 214 (M++H, 100.

Provenance & Evidence