Hydrogen Peroxide → HCID 15728606, compound

HRID 1197049Notes

Reaction equation

HRID 1197049 reaction equation
[CH3:1][Si:2]([CH3:22])([CH3:21])[O:3][C:4]1([CH2:10][CH2:11][CH2:12][CH2:13][O:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH2:8][C:7](=[O:9])[CH:6]=[CH:5]1.[OH:23]O.[OH-:25].[Na+].[Cl-].[NH4+]>CO>[O:23]1[CH:5]2[CH:6]1[C:7](=[O:9])[CH2:8][C:4]2([O:3][Si:2]([CH3:1])([CH3:21])[CH3:22])[CH2:10][CH2:11][CH2:12][CH2:13][O:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.[O:25]1[CH:5]2[CH:6]1[C:7](=[O:9])[CH2:8][C:4]2([OH:3])[CH2:10][CH2:11][CH2:12][CH2:13][O:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

7

Reactant 4

HCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 25517Ammonium ChlorideHCID 14837915HCID 14837915, compound

Product 2

HCID 15728606HCID 15728606, compoundYield 53%HCID 15728607HCID 15728607, compoundYield 34%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 2.49 g of 4-trimethylsilyloxy-4-(4-phenoxybutyl)-2-cyclopentenone dissolved in 50 ml of methanol was added 3.9 ml of an aqueous 30% hydrogen peroxide under ice-cooling and stirring. An amount of 390 μl of 1N aqueous sodium hydroxide was added, and the mixture was stirred for 2 hours. Then saturated aqueous ammonium chloride was added, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium chloride and dried over anhydrous magnesium sulfate. After filtration and concentration, the concentrate was subjected to silica gel column chromatography to give 892 mg (yield 34%) of 2,3-epoxy-4-trimethylsilyloxy-4-(4-phenoxybutyl)cyclopentanone and 1.38 g (yield 53%) of 2,3-epoxy-4-hydroxy-4-(4-phenoxybutyl)cyclopentanone.

Workup

  1. temperaturecooling
  2. stirringthe mixture was stirred for 2 hours
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with saturated aqueous sodium chloride
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationAfter filtration and concentration

Sources & evidence

ORD record
ord-d64c022250344d96924afb133a07ccf8
Source dataset
uspto-grants-1992_05
Patent number
US05116869

Reaction notes

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