HCID 10986966, compound → HCID 12838012, compound

HRID 2163171Notes

Reaction equation

HRID 2163171 reaction equation
[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][C@@H:8]1[CH:12]=[CH:11][C@@H:10]([OH:13])[CH2:9]1>C1C=CC=CC=1.[O-2].[O-2].[Mn+4]>[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][C@H:8]1[CH2:9][C:10](=[O:13])[CH:11]=[CH:12]1

Participants

4

Reactant 1

HCID 10986966HCID 10986966, compound

Product 1

HCID 12838012HCID 12838012, compoundYield 67.4%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 241BenzeneSolvent

Procedure

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.

Workup

  1. temperaturethe resulting solution was refluxed
  2. customSix hours later, the resulting precipitate was separated by filtration
  3. distillationafter distilling off the organic solvent
  4. custompurified by thin-layer chromatography (cyclohexane-ethyl acetate = 7:3)

Sources & evidence

ORD record
ord-ea6b02d0c3ef41eca9dfa3fd448f98f9
Source dataset
uspto-grants-1979_01
Patent number
US04132726

Reaction notes

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