Sodium hydride → HCID 53482062, Verbindung

HRID 260707

Reaktionsgleichung

Reaktionsgleichung von HRID 260707
[F:1][C:2]1[CH:3]=[C:4]([OH:9])[CH:5]=[CH:6][C:7]=1[F:8].[H-].[Na+].CC1C=CC(S(O[CH2:23][C@@H:24]2[CH2:26][O:25]2)(=O)=O)=CC=1>CN(C)C=O>[F:1][C:2]1[CH:3]=[C:4]([CH:5]=[CH:6][C:7]=1[F:8])[O:9][CH2:23][C@@H:24]1[CH2:26][O:25]1

Komponenten

5

Edukt 3

HCID 24758Sodium hydrideHCID 759273,4-DifluorophenolHCID 153296Oxiranemethanol, 4-methylbenzenesulfonate, (S)-

Produkt 1

HCID 53482062HCID 53482062, VerbindungAusbeute 51,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel2×

Versuchsvorschrift

To a stirred and cooled (ice-bath) mixture of 13.0 g of 3,4-difluorophenol and 200 ml of N,N-dimethylformamide, there were added 4.8 g of a dispersion of sodium hydride in mineral oil (50%) and, after stirring for 1 hour, a solution of 22.8 g of (S)-(oxiranylmethyl) 4-methylbenzenesulfonate (ester) in some N,N-dimethylformamide. Stirring at room temperature was continued overnight. The reaction mixture was poured into ice-water and the product was extracted with methylbenzene. The extract was washed with NaCl (dil.) and water and was then dried, filtered and evaporated. The residue was distilled (13.3 Pa, 55° C.), yielding 9.5 g (51.0%) of (S)-[(3,4-difluorophenoxy)methyl]oxirane (interm. 1 ).

Aufarbeitung

  1. temperaturecooled
  2. stirringafter stirring for 1 hour
  3. stirringStirring at room temperature
  4. extractionthe product was extracted with methylbenzene
  5. washThe extract was washed with NaCl (dil.) and water
  6. customwas then dried
  7. filtrationfiltered
  8. customevaporated
  9. distillationThe residue was distilled (13.3 Pa, 55° C.)

Quellen und Nachweise

ORD-Eintrag
ord-f4c0909046dc4f19bd7e05b9176bdb8d
Quelldatensatz
uspto-grants-1996_06
Patentnummer
US05530011

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