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

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).

1. custompurged under nitrogen
2. additionPalladium on carbon (5%, 200 mg) was then added
3. filtrationThe reaction mixture was filtered over CELITE
4. washrinsed with ethanol
5. concentrationconcentrated under reduced pressure
6. customThe residue was purified by column chromatography on silica gel (5 to 30% EtOAc/hexanes)

ORD record

ord-548681de6ecf476bb6684ed4cbec266e

Source dataset

uspto-grants-2016_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09242984B2