2,6-Dimethyl-4-pyranone → cis-2,6-dimethyloxan-4-one

Participants

Reaction Steps

2,6-Dimethyl-4H-pyran-4-one (2.0 g, 16 mmol) was dissolved in ethanol (10 mL) and purged under nitrogen. Palladium on carbon (5%, 200 mg) was then added and the reaction mixture stirred under hydrogen gas (40 psi) for 24 hours. The reaction mixture was filtered over CELITE, rinsed with ethanol, and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (5 to 30% EtOAc/hexanes) to afford cis-2,6-dimethyltetrahydro-4H-pyran-4-one as a colorless liquid. 1H NMR (500 MHz, CDCl3) δ 3.77-3.70 (m, 2H), 2.38-2.32 (m, 2H), 2.25-2.20 (m, 2H), 1.32 (d, J=6.1 Hz, 6H).

Provenance & Evidence