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

Participants

Reaction Steps

A solution of 3-(1,4-dioxa-spiro[4,5]dec-8-yl)-5-cyano-1-methyl-indole (5.5 g) in 150 ml (1:1) tetrahydrofuran-hydrochloric acid (1N) was allowed to stir at room temperature for 16 hours, followed by the addition of 4.49 g sodium bicarbonate. The mixture was extracted with methylene chloride (3×100 ml), 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 to afford 2.06 g of the title compound as a solid: mp 150-152° C.

Provenance & Evidence