Sodium Chloride → 3-Furyl 4-Methyl-5-oxazolyl Ketone

HRID 975036

Reaktionsgleichung

Reaktionsgleichung von HRID 975036
Br[C:2]1[CH:6]=[CH:5][O:4][CH:3]=1.C([Li])CCC.CON(C)[C:15]([C:17]1[O:21][CH:20]=[N:19][C:18]=1[CH3:22])=[O:16].[Cl-].[Na+]>C(OCC)C.C(O)C>[CH3:22][C:18]1[N:19]=[CH:20][O:21][C:17]=1[C:15]([C:2]1[CH:6]=[CH:5][O:4][CH:3]=1)=[O:16]

Komponenten

7

Edukt 4

HCID 5234Sodium ChlorideHCID 891643-BromofuranHCID 18925369N-Methoxy-N,4-dimethyloxazole-5-carboxamideHCID 178418339Butyllithium

Produkt 1

HCID 189363073-Furyl 4-Methyl-5-oxazolyl Ketone

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 3283Diethyl EtherLösungsmittel2×

Reaktionsbedingungen

Temperatur
-70 °C

Versuchsvorschrift

3-Bromofuran (2.5 g) in dry diethylether was stirred and cooled to -70° C. under an atmosphere of dry nitrogen and n-butyllithium (2.5M solution in hexane, 6.8 ml) was added dropwise. After 30 minutes, N-methoxy-N-methyl-4-methyl-5-oxazolecarboxamide (2.89 g) in dry diethylether was added dropwise. After a further 30 minutes the mixture was allowed to warm to room temperature. Ethanol (5 ml) was added followed by saturated aqueous sodium chloride. The mixture was extracted with dichloromethane and the material thus obtained was purified by flash chromatography to give the title compound. M.p. 82°-83.5° C.

Aufarbeitung

  1. waitAfter a further 30 minutes the mixture was allowed
  2. temperatureto warm to room temperature
  3. extractionThe mixture was extracted with dichloromethane
  4. customthe material thus obtained
  5. customwas purified by flash chromatography

Quellen und Nachweise

ORD-Eintrag
ord-980b194ef9ec45299c81e378f17749bd
Quelldatensatz
uspto-grants-1997_03
Patentnummer
US05607956

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