Methyl iodide → 2-Hydroxyquinoline

Participants

Reaction Conditions

Reaction Steps

A 10-mL RBF was charged with 6-(benzylthio)-1-((1R,2R)-2-hydroxycyclohexyl)quinolin-2(1H)-one (150 mg, 0.410 mmol) and purged with nitrogen for 10 min. TI-IF (2.1 mL) was introduced and the resultant solution cooled to −78° C. A solution of potassium bis(trimethylsilyl)amide in tetrahydrofuran (1.0M, 451 μl, 0.451 mmol) was added dropwise to the stirred reaction mixture over 2 min via syringe to produce a dark purple solution. After 15 min, iodomethane (28.0 μl, 0.451 mmol) was added dropwise via syringe and the resultant reaction mixture was allowed to warm to 0° C. After 15 min, a solution of saturated aqueous ammonium chloride was added and the reaction mixture was allowed to warm to ambient temperature and diluted with EtOAc (10 mL). The layers were separated, and the aqueous layer was further extracted with. EtOAc (3×10 mL). The combined organic layers were then washed with brine (20 mL), dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by flash column chromatography (25-g Biotage column, eluent: gradient, 0 to 20% EtOAc in heptane) to afford (±)-6-(benzylthio)-141R,2R)-2-methoxycyclohexyl)quinolin-2(1H)-one (119 mg, 0.314 mmol, 76% yield) as a yellow solid. m/z (ESI) 380.2 (M+H)+.

Provenance & Evidence