반응 #2250353

반응 방정식

(S)-trans-5-tetrahydropyranyloxycyclopent-1-en-3-ol

→

(S)-4-tetrahydropyranyloxycyclopent-2-en-1-one

수율 67.4%

용매

—

petroleum ether

benzene

반응 조건

후처리

1. 1
   온도the resulting solution was refluxed
2. 2
   기타Six hours later, the resulting precipitate was separated by filtration
3. 3
   workup.DISTILLATIONafter distilling off the organic solvent
4. 4
   기타purified by thin-layer chromatography (cyclohexane-ethyl acetate = 7:3)

실험 절차

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.

출처