Formamide → 4-Phenyl-1,3-oxazole

HRID 1944709

Reaktionsgleichung

Reaktionsgleichung von HRID 1944709
Br[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=O.[CH:11]([NH2:13])=[O:12]>C(OCC)(=O)C.O>[C:5]1([C:3]2[N:13]=[CH:11][O:12][CH:2]=2)[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

Komponenten

5

Edukt 2

HCID 713FormamideHCID 6259Phenacyl bromide

Produkt 1

HCID 5892794-Phenyl-1,3-oxazoleAusbeute 39,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
130 °C

Versuchsvorschrift

Bromoacetophenone (595 mg, 2.99 mmol) and formamide (1781 μl, 44.8 mmol) were combined and heated at 130° C. for 90 min. The reaction was cooled then dilute with ethyl acetate and water and extracted with ethyl acetate. The organic layer was dried over sodium sulfate, filtered, and concentrated. The concentrate was purified by chromatography on a Biotage 25M column using a 5-8% ethyl acetate in heptane gradiant to yield 4-phenyl-oxazole (170 mg, 1.17 mmol). TLC (5% ethyl acetate in heptane) of product: Rf=0.28.

Aufarbeitung

  1. temperatureThe reaction was cooled
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe concentrate was purified by chromatography on a Biotage 25M column

Quellen und Nachweise

ORD-Eintrag
ord-052b546579ef47e1bf8a809b91d1baf8
Quelldatensatz
uspto-grants-2013_03
Patentnummer
US08394858B2

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