HCID 70607943, compound → (4R)-4-[(Oxan-2-yl)oxy]cyclopent-2-en-1-one

HRID 2163170Notes

Reaction equation

HRID 2163170 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 70607943HCID 70607943, compound

Product 1

HCID 12838011(4R)-4-[(Oxan-2-yl)oxy]cyclopent-2-en-1-oneYield 67.4%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 241BenzeneSolvent

Procedure

Six milligrams of (R)-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 (R)-4-tetrahydropyranyloxycyclopent-2-en-1-one.

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-930d29d5a26544d88be1b6f07a863795
Source dataset
uspto-grants-1979_01
Patent number
US04132726

Reaction notes

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