Water → 4-Phenyl-1,3-oxazole

HRID 2399913

Reaktionsgleichung

Reaktionsgleichung von HRID 2399913
Br[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=O.[CH:11]([O-:13])=O.[NH4+:14].O>C(O)=O>[C:5]1([C:3]2[N:14]=[CH:11][O:13][CH:2]=2)[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

Komponenten

5

Edukt 3

HCID 962WaterHCID 6259Phenacyl bromideHCID 2723923Ammonium formate

Produkt 1

HCID 5892794-Phenyl-1,3-oxazoleAusbeute 31 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 284Formic AcidLösungsmittel

Versuchsvorschrift

A mixture of 2-bromoacetophenone and ammonium formate in formic acid was stirred at reflux under nitrogen for 2 hours. The cooled reaction mixture was treated with 400 mL of H2O and extracted with ether (3×200 mL). The combined organics were washed with saturated aqueous NaHCO3, dried over MgSO4, filtered and concentrated under reduced pressure. The residue was purified by column chromatography (eluting with EtOAc/hexanes, 1:9) to afford 8.9 g (31%) of 4-phenyloxazole as a yellow oil.

Aufarbeitung

  1. temperatureat reflux under nitrogen for 2 hours
  2. customThe cooled reaction mixture
  3. extractionextracted with ether (3×200 mL)
  4. washThe combined organics were washed with saturated aqueous NaHCO3
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by column chromatography (eluting with EtOAc/hexanes, 1:9)

Quellen und Nachweise

ORD-Eintrag
ord-d210e6dcc0614ccab50e24bcaaf1dcbc
Quelldatensatz
uspto-grants-1995_09
Patentnummer
US05451686

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