Hydrogen Peroxide → HCID 86663676, compound

HRID 1193248Notes

Reaction equation

HRID 1193248 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:19][CH:20]([F:22])[F:21])=[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:23]O>CO.[OH-].[Li+]>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:19][CH:20]([F:22])[F:21])=[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:23]2)[CH:7]=1

Participants

5

Reactant 2

HCID 784Hydrogen PeroxideHCID 66823734HCID 66823734, compound

Product 1

HCID 86663676HCID 86663676, compoundYield 80.2%

Reagents, catalysts & solvents 2

HCID 3939Lithium HydroxideCatalystHCID 887MethanolSolvent

Procedure

To a solution of 4-[1-(5-bromo-2-difluoromethoxyphenyl)methylidene]-2,2,5,5-tetramethyldihydrofuran-3-one (8.89 g, 0.023 mol) in methanol (380 ml) at 35° C. is added 50% aqueous hydrogen peroxide (2.30 ml, 0.034 mol), immediately followed by 2M aqueous lithium hydroxide (2.30 ml, 0.0046 mmol). After stirring at this temperature for 1 hour the reaction mixture is allowed to cool, then quenched with 10% sodium metabisulfite solution (negative KI-starch indicator test). The reaction mixture is extracted with diethyl ether (×3), then the organic phase is further washed with saturated aqueous sodium bicarbonate (×2) then brine. All organics are combined, dried over magnesium sulfate, filtered and the filtrate concentrated in vacuo to afford 2-(5-bromo-2-difluoromethoxyphenyl)-4,4,6,6-tetramethyl-1,5-dioxaspiro[2.4]heptan-7-one (7.22 g) a yellow gum.

Workup

  1. temperatureto cool
  2. customquenched with 10% sodium metabisulfite solution (negative KI-starch indicator test)
  3. extractionThe reaction mixture is extracted with diethyl ether (×3)
  4. washthe organic phase is further washed with saturated aqueous sodium bicarbonate (×2)
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationthe filtrate concentrated in vacuo

Sources & evidence

ORD record
ord-12d569862f3546d5ba52f54fe01210a9
Source dataset
uspto-grants-2014_03
Patent number
US08680299B2

Reaction notes

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