Hydrogen Peroxide → HCID 58061055, compound

HRID 537686Notes

Reaction equation

HRID 537686 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH:19]2[CH2:21][CH2:20]2)=[C:6]([CH:8]=[C:9]2[C:13]([CH3:15])([CH3:14])[O:12][C:11]([CH3:17])([CH3:16])[C:10]2=[O:18])[CH:7]=1.[OH-:22].[Li+].OO>CO>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH:19]2[CH2:21][CH2:20]2)=[C:6]([CH:8]2[C:9]3([C:10](=[O:18])[C:11]([CH3:17])([CH3:16])[O:12][C:13]3([CH3:14])[CH3:15])[O:22]2)[CH:7]=1

Participants

5

Reactant 3

HCID 784Hydrogen PeroxideHCID 3939Lithium HydroxideHCID 66679939HCID 66679939, compound

Product 1

HCID 58061055HCID 58061055, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
45 °C

Procedure

To a solution of 4-[1-(5-bromo-2-cyclopropylphenyl)methylidene]-2,2,5,5-tetramethyldihydrofuran-3-one (189 g, 541 mmol) in methanol (2650 ml) at 53° C. is added and 2M aqueous lithium hydroxide (27.1 ml, 54.2 mmol) then 50% aqueous hydrogen peroxide (46.1 ml, 812 mmol). After stirring for 30 minutes at this temperature the solution is cooled to 45° C. and quenched with saturated aqueous sodium thiosulfate. Distilled water (1000 ml) is added and the organic solvents are removed in vacuo. The aqueous phase is then extracted into ethyl acetate (×2) and the combined organic extracts are washed with saturated aqueous sodium hydrogen carbonate (×2), brine (500 mL), then dried over anhydrous magnesium sulfate. Volatile solvents are removed under vacuum to afford 2-(5-bromo-2-cyclopropylphenyl)-4,4,6,6-tetramethyl-1,5-dioxaspiro[2.4]heptan-7-one.

Workup

  1. customquenched with saturated aqueous sodium thiosulfate
  2. additionDistilled water (1000 ml) is added
  3. customthe organic solvents are removed in vacuo
  4. extractionThe aqueous phase is then extracted into ethyl acetate (×2)
  5. washthe combined organic extracts are washed with saturated aqueous sodium hydrogen carbonate (×2), brine (500 mL)
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customVolatile solvents are removed under vacuum

Sources & evidence

ORD record
ord-c24fbbb6e9574d1194a9663eebadf05f
Source dataset
uspto-grants-2014_10
Patent number
US08865623B2

Reaction notes

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