Hydrogen Peroxide → (R)-4-(tert-Butyldimethylsilanyloxy)-6-oxabicyclo[3.1.0]hexan-2-one

HRID 2187965Notes

Reaction equation

HRID 2187965 reaction equation
[OH:1]O.[OH-].[Na+].[Si:5]([O:12][C@@H:13]1[CH2:17][C:16](=[O:18])[CH:15]=[CH:14]1)([C:8]([CH3:11])([CH3:10])[CH3:9])([CH3:7])[CH3:6]>CO>[Si:5]([O:12][CH:13]1[CH:17]2[C@@H:16]([O:18]2)[C:15](=[O:1])[CH2:14]1)([C:8]([CH3:11])([CH3:10])[CH3:9])([CH3:7])[CH3:6]

Participants

5

Reactant 3

HCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 2734530(4R)-(+)-t-Butyldimethylsiloxy-2-cyclopenten-1-one

Product 1

HCID 86587272(R)-4-(tert-Butyldimethylsilanyloxy)-6-oxabicyclo[3.1.0]hexan-2-one

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

Hydrogen peroxide (4.5 mL, 46.3 mmol, 30% by wt.) and 1N NaOH (46 μL, 0.046 mmol) were added to a solution of enone 2 (2.5 g, 11.5 mmol) in MeOH (30 mL) at 0° C. After stirring 1.5 h at 0° C. the mixture was concentrated in vacuo, washed with saturated aqueous NH4Cl and extracted with CH2Cl2 (3×). The combined organics were washed with brine, dried (Na2SO4), filtered and concentrated in vacuo to afford the above titled compound.

Workup

  1. concentrationwas concentrated in vacuo
  2. washwashed with saturated aqueous NH4Cl
  3. extractionextracted with CH2Cl2 (3×)
  4. washThe combined organics were washed with brine
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-02c255224f75442a9f455a8d0e694af2
Source dataset
uspto-grants-2002_06
Patent number
US06410591B1

Reaction notes

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