Mandelic Acid → HCID 12390395, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of hydroxy-phenyl-acetic acid (2 g, 13.4 mmol) in DCM (30 mL) was added PTSA (51.2 mg, 0.27 mmol) at 0° C. followed by the addition of 3,4-dihydro-2H-pyran (1.55 g, 18.4 mmol). The mixture was stirred at 0° C. for another 15 min and then gradually warmed up to room temperature and stirred for a further 1.5 hours. The reaction mixture was diluted with DCM (100 mL). The organic phase was washed with saturated aq. Na2CO3 (2×20 mL), water (20 mL), brine (20 mL), dried (Na2SO4) and evaporated in vacuo. The crude material was purified by column chromatography on silica gel (EtOAc:petroleum ether 2:5) to afford the title compound as a yellow sticky solid in 48% yield, 1.5 g. LCMS (system 10): Rt=1.82 min; m/z 237 [M+H]+.

Provenance & Evidence