Sodium Methoxide → HCID 117737100, compound

Participants

Reaction Conditions

Reaction Steps

A 25-mL pressure vessel was charged with (E)-ethyl 3-(5-(benzylthio)-2-((2-hydroxycyclohexyl)amino)phenyl)acrylate (2.36 g, 5.73 mmol), methanol (10 ml), and a solution of sodium methoxide in methanol (25 wt. %, 2.64 mL, 11.47 mmol). The reaction vessel was sealed with a Teflon cap and the yellow reaction mixture was warmed to 70° C. After 16 h, additional solution of sodium methoxide in methanol (25 wt. %, 1.9 mL, 8.25 mmol) was added and the reaction vessel was sealed and warmed to 100° C. After 20 h, the reaction mixture was allowed to cool to ambient temperature and concentrated under reduced pressure to furnish a yellow residue which was purified by flash column chromatography (50-g Biotage column, eluent: gradient, 20 to 70% EtOAc in heptane) to afford 6-(benzylthio)-1-((1R,2R)-2-hydroxycyclohexyl)quinolin-2(1H)-one (469 mg, 1.283 mmol, 22.38% yield) as a yellow syrup. m/z (ESI) 366.1 (M+H)+.

Provenance & Evidence