Hydrogen Peroxide → 2,3-Epoxy-4-(2-tetrahydropyranyloxy)cyclopentan-1-one

HRID 1448632

Reaction equation

HRID 1448632 reaction equation
[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][CH:8]1[CH2:12][C:11](=[O:13])[CH:10]=[CH:9]1.OO.[OH-].[Na+].[O:18](C1CC(=O)C(SCCCCCCCC)=C1)[Si](C(C)(C)C)(C)C>CO>[O:13]1[CH:12]2[CH:11]1[C:10](=[O:18])[CH2:9][CH:8]2[O:7][CH:2]1[CH2:3][CH2:4][CH2:5][CH2:6][O:1]1

Participants

6

Reactant 4

HCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 128380104-(Tetrahydro-pyran-2-yloxy)-cyclopent-2-enoneHCID 203803744-t-Butyldimethylsiloxy-2-n-octylthiocyclopent-2-en-1-one

Product 1

HCID 203803472,3-Epoxy-4-(2-tetrahydropyranyloxy)cyclopentan-1-oneYield 84%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

One gram of 4-(2-tetrahydropyranyloxy)cyclopent-2-en-1-one was dissolved in 20 ml of methanol, and 10 ml of 30% hydrogen peroxide was added at room temperature. Then, with ice cooling, 3 ml of a 2 N aqueous solution of sodium hydroxide was added slowly. The mixture was stirred at room temperature for 1.5 hours. The reaction mixture was post-treated in the same way as in Example 1, (1). The resulting crude product was chromatographed on a thin layer plate with cyclohexane/ethyl acetate (=7/3) to afford 730 mg of 2,3-epoxy-4-(2-tetrahydropyranyloxy)cyclopentan-1-one in a yield of 84%. The product had the following spectral data.

Workup

  1. customThe resulting crude product was chromatographed on a thin layer plate with cyclohexane/ethyl acetate (=7/3)

Sources & evidence

ORD record
ord-5f425e3822f0430cbb3da60d10d1f887
Source dataset
uspto-grants-1979_12
Patent number
US04180672

Linked notes

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