Sulfoxonium, trimethyl-, iodide (1:1) → 2-[2-(5-Fluoro-2-methoxyphenyl)-2-methylpropyl]-2-difluoromethyloxirane

HRID 2106056Notes

Reaction equation

HRID 2106056 reaction equation
[I-].C[S+](C)(C)=O.[CH3:7][Si](C)(C)[N-][Si](C)(C)C.[Na+].[F:17][CH:18]([F:34])[C:19](=[O:33])[CH2:20][C:21]([CH3:32])([C:23]1[CH:28]=[C:27]([F:29])[CH:26]=[CH:25][C:24]=1[O:30][CH3:31])[CH3:22]>CS(C)=O.C1COCC1.CCCCCC>[F:29][C:27]1[CH:26]=[CH:25][C:24]([O:30][CH3:31])=[C:23]([C:21]([CH3:22])([CH3:32])[CH2:20][C:19]2([CH:18]([F:17])[F:34])[CH2:7][O:33]2)[CH:28]=1

Participants

7

Reactant 3

HCID 74498Sulfoxonium, trimethyl-, iodide (1:1)HCID 2724254Sodium bis(trimethylsilyl)amideHCID 578099691,1,-Difluoro-4-methyl-4-(2-methoxy-5-fluorophenyl)pentan-2-one

Product 1

HCID 578097912-[2-(5-Fluoro-2-methoxyphenyl)-2-methylpropyl]-2-difluoromethyloxirane

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolventHCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Procedure

To suspension of trimethylsulfoxonium iodide (0.22 g) in DMSO (0.5 mL) and THF (0.5 mL) stirred under nitrogen and cooled on ice was added sodium hexamethyldisilazide (1.0 mL, 1.0M in THF) dropwise over 5 minutes. After 15 minutes, a solution of 1,1,-difluoro-4-methyl-4-(2-methoxy-5-fluorophenyl)pentan-2-one (0.23 g) in THF (0.6 mL) was added dropwise and the mixture was allowed to come to room temperature over 2 hours. The mixture was diluted with hexane, washed with water, dried, filtered, and evaporated in vacuo to give 2-[2-(5-fluoro-2-methoxyphenyl)-2-methylpropyl]-2-difluoromethyloxirane as an oil (0.25 g).

Workup

  1. temperaturecooled on ice
  2. waitto come to room temperature over 2 hours
  3. washwashed with water
  4. customdried
  5. filtrationfiltered
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-240c321e287443fcaf539439071c1bc4
Source dataset
uspto-grants-2009_08
Patent number
US07579469B2

Reaction notes

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