2,6-Dimethyl-4-pyranone → (2R,6S)-2,6-dimethyloxan-4-one

Participants

Reaction Steps

2,6-Dimethyl-4H-pyran-4-one (10 g, 81 mmol) was dissolved in ethanol (125 mL) and Pd/C (1 g, 0.94 mmol) was added. The mixture was hydrogenated in a Parr shaker under H2 (0.325 g, 161 mmol) (70 psi) at room temperature for 12 hrs. The catalyst was filtered through a pad of CELITE® and washed with ethanol. The filtrate was concentrated in vacuum and the residue was purified via BIOTAGE® (2% to 25% EtOAc/Hex; 160 g column). Two fractions of clear oils were isolated. The first eluting one corresponded to (2R,6S)-2,6-dimethyldihydro-2 H-pyran-4(3 H)-one (1.8 g, 14.04 mmol, 17.43% yield) while the second one corresponded to Cap-179, step a (1.8 g).

Provenance & Evidence