Hydrochloric Acid → HCID 21107254, compound

Participants

Reaction Steps

A solution of 8-ethyl-4,4-dimethyl-6-methoxy-3,4-dihydro-2H-naphthalen-1-one (Intermediate 176, 1.1 g, 4.73 mmol) and sodium cyanide (1.6 g, 33 mmol) in anhydrous dimethylsulfoxide (20 mL) was heated at 210° C. overnight under argon. The reaction mixture was then cooled to ambient temperature, poured into ice and acidified (Caution! Hydrogen cyanide evolution!) using 10% hydrochloric acid and extracted with ethyl acetate. The combined organic extract was washed with brine (×1), dried over anhydrous sodium sulfate, filtered and evaporated to afford a dark orange solid. Flash column chromatography on silica gel (230-400 mesh) using 10-20% ethyl acetate in hexane as the eluent afforded the title compound as a yellow solid (0.82 g, 82%).

Provenance & Evidence