Selenium Dioxide → 6-Fluoroquinoxaline-2-carbaldehyde

HRID 2302073Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2302073
[CH3:1][C:2]1[CH:11]=[N:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([F:12])[CH:8]=2)[N:3]=1.[Se](=O)=[O:14]>C(OCC)(=O)C>[F:12][C:7]1[CH:8]=[C:9]2[C:4](=[CH:5][CH:6]=1)[N:3]=[C:2]([CH:1]=[O:14])[CH:11]=[N:10]2

Komponenten

4

Edukt 2

HCID 24007Selenium DioxideHCID 133808502-Methyl-6-fluoroquinoxaline

Produkt 1

HCID 221364416-Fluoroquinoxaline-2-carbaldehydeAusbeute 29 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

Using the method of Kepez (Monatahefte fur Chemie, 1989, 120, 127-130), a solution of 2-methyl-6-fluoroquinoxaline (225 mg 1.39 mmol) in ethyl acetate (30 mL) was treated with selenium dioxide (2.5 g) and the reaction mixture heated at reflux for 36 hours. The reaction was filtered hot and concentrated. Chromatography through a Biotage silica cartridge (8×4 cm i.d.) using a gradient of hexane to 10% ethyl acetate (in hexane) afforded 71 mg (29%) of 6-fluoroquinoxaline-2-carboxaldehyde.

Aufarbeitung

  1. temperaturethe reaction mixture heated
  2. temperatureat reflux for 36 hours
  3. filtrationThe reaction was filtered hot
  4. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-a6bdfb92793b42bd89cb82be23e9653e
Quelldatensatz
uspto-grants-2002_08
Patentnummer
US06429207B1

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