HCID 10986966, compound → HCID 12838012, compound

Participants

Reaction Steps

Six milligrams of (S)-trans-5-tetrahydropyranyloxycyclopent-1-en-3-ol was dissolved in a solvent mixture of 3 milliliters of petroleum ether and 0.5 milliliter of benzene, and the resulting solution was refluxed after the addition of 10 milligrams of active manganese dioxide. Six hours later, the resulting precipitate was separated by filtration and, after distilling off the organic solvent, purified by thin-layer chromatography (cyclohexane-ethyl acetate = 7:3) to obtain 4 milligrams (67%) of (S)-4-tetrahydropyranyloxycyclopent-2-en-1-one. The IR and NMR data were in complete agreement with those of the corresponding (R)-isomer.

Provenance & Evidence