Hydrogen Peroxide → 2,3-Epoxy-4-octyl-4-trimethylsilyloxycyclopentanone

HRID 1587131Notes

Reaction equation

HRID 1587131 reaction equation
[CH2:1]([C:9]1([O:15][Si:16]([CH3:19])([CH3:18])[CH3:17])[CH2:13][C:12](=[O:14])[CH:11]=[CH:10]1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].[OH:20]O.[OH-].[Na+].[Cl-].[NH4+]>CO>[O:14]1[CH:13]2[CH:12]1[C:11](=[O:20])[CH2:10][C:9]2([CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8])[O:15][Si:16]([CH3:19])([CH3:18])[CH3:17]

Participants

6

Reactant 4

HCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 25517Ammonium ChlorideHCID 137677604-Octyl-4-trimethylsilyloxy-2-cyclopentenone

Product 1

HCID 197605912,3-Epoxy-4-octyl-4-trimethylsilyloxycyclopentanone

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 3.3 g of 4-octyl-4-trimethylsilyloxy-2-cyclopentenone dissolved in 50 ml of methanol was added, under ice-cooling and stirring, 5.0 ml of an aqueous 30% hydrogen peroxide, and 500 μl of an aqueous 1N sodium hydroxide was added. After the mixture was stirred for 3.5 hours, 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. The product was filtered and concentrated to give a crude oil of 2,3-epoxy-4-octyl-4-trimethylsilyloxycyclopentanone.

Workup

  1. additionwas added, under ice-
  2. temperaturecooling
  3. stirringAfter the mixture was stirred for 3.5 hours
  4. extractionthe mixture was extracted with ethyl acetate
  5. washThe organic layer was washed with saturated aqueous sodium chloride
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationThe product was filtered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-096f1f93eb7945a78001cf724db05b2c
Source dataset
uspto-grants-1993_06
Patent number
US05216183

Reaction notes

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