Sodium Bicarbonate → 4-(5-Cyano-1-methyl-3-indolyl)cyclohexanone

Participants

Reaction Steps

A solution of 4-(5-cyano-1-methyl-3-indolyl)-cyclohexanone ethylene ketal (5.5 g) in 150 ml (1:1) tetrahydrofuran-hydrochloric acid (1N) was allowed to stir at room temperature for 16 hours, then to above solution sodium bicarbonate (4.49 g) was added. The mixture was extracted with methylene chloride (3×100 ml) and washed with brine (3×150 ml). The organic layer was dried over anhydrous magnesium sulfate and filtered. The solvent was removed to afford a light brown solid which was boiled in ethyl acetate-hexanes (1:1). The mixture was cooled to room temperature and solid was collected and dried under vacuum (2.06 g): mp 150-152° C.

Provenance & Evidence