Dimethyl Sulfoxide → 1-(2-Acetoxyethyl)thio-2-(2,4-difluorophenyl)-1,1-difluoro-2,3-epoxypropane

HRID 1585661Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1585661
[H-].[Na+].[CH3:3]S(C)=O.[I-].C[S+](C)(C)=O.[C:13]([O:16][CH2:17][CH2:18][S:19][C:20]([F:32])([F:31])[C:21]([C:23]1[CH:28]=[CH:27][C:26]([F:29])=[CH:25][C:24]=1[F:30])=[O:22])(=[O:15])[CH3:14]>C1COCC1>[C:13]([O:16][CH2:17][CH2:18][S:19][C:20]([F:31])([F:32])[C:21]1([C:23]2[CH:28]=[CH:27][C:26]([F:29])=[CH:25][C:24]=2[F:30])[O:22][CH2:3]1)(=[O:15])[CH3:14]

Komponenten

6

Edukt 4

HCID 679Dimethyl SulfoxideHCID 24758Sodium hydrideHCID 74498Sulfoxonium, trimethyl-, iodide (1:1)HCID 10710064HCID 10710064, Verbindung

Produkt 1

HCID 107110891-(2-Acetoxyethyl)thio-2-(2,4-difluorophenyl)-1,1-difluoro-2,3-epoxypropaneAusbeute 90 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

A suspension of 60% NaH (3.95 g, 0.1 mol) in THF (60 ml)-DMSO (120 ml) was heated to an external temperature of 50° C., followed by the addition of trimethylsulfoxonium iodide (21.7 g, 0.1 mol) in portions. The resulting mixture was stirred for 15 minutes at the same temperature and was then cooled to -20° C. To the reaction mixture, a solution of 2-(2-acetoxyethyl)thio-2,2-difluoro-2',4'-difluoroacetophenone (25.5 g, 0.08 mol) in THE (60 ml) was added dropwise. After being stirred at room temperature for 1.5 hours, the reaction mixture was poured into ice water, followed by extraction with ethyl ether. The ether solution was washed with water, dried over magnesium sulfate and then distilled off under reduced pressure, whereby 1-(2-acetoxyethyl)thio-2-(2,4-difluorophenyl)-1,1-difluoro-2,3-epoxypropane (24.0 g, yield: 90.0%) was obtained as a pale yellow oil.

Aufarbeitung

  1. temperaturewas then cooled to -20° C
  2. stirringAfter being stirred at room temperature for 1.5 hours
  3. extractionfollowed by extraction with ethyl ether
  4. washThe ether solution was washed with water
  5. dry with materialdried over magnesium sulfate
  6. distillationdistilled off under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-5b66a21faf3c4d109d049328ab5e2b3d
Quelldatensatz
uspto-grants-1999_08
Patentnummer
US05939448

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