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

HRID 2106056Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2106056
[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

Komponenten

7

Edukt 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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 679Dimethyl SulfoxideLösungsmittelHCID 8028TetrahydrofuranLösungsmittel2×HCID 8058HexaneLösungsmittel

Versuchsvorschrift

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).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-240c321e287443fcaf539439071c1bc4
Quelldatensatz
uspto-grants-2009_08
Patentnummer
US07579469B2

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