Reaktion #82821

Reaktionsgleichung

4-nitrobenzamide oxime

ethyl chlorooxoacetate

borontrifluoride

→

5-ethoxycarbonyl-3-(4-nitrophenyl)-1,2,4-oxadiazole

Lösungsmittel

dioxane

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturwas refluxed for 1 hour
2. 2
   TemperaturThe whole mixture was refluxed for 12 hours
3. 3
   Sonstigethe solvent was evaporated in vacuo
4. 4
   workup.ADDITIONThe residue was diluted with ethyl acetate (100 ml)
5. 5
   Waschenwashed with a saturated potassium carbonate aqueous solution
6. 6
   Trocknendried over magnesium sulfate
7. 7
   Sonstigeevaporated in vacuo
8. 8
   SonstigeThe residue was purified by column chromatography on silica gel with a mixture of dichloromethane and hexane (1:1) as eluent
9. 9
   workup.ADDITIONThe fractions containing the object product
10. 10
    Sonstigewere collected
11. 11
    Sonstigeevaporated in vacuo

Vorschrift

A mixture of 4-nitrobenzamide oxime (4 g) and ethyl chlorooxoacetate (3.01 g) in dioxane (200 ml) was refluxed for 1 hour, and then borontrifluoride (1 ml) was added thereto. The whole mixture was refluxed for 12 hours. After being cooled to room temperature, the solvent was evaporated in vacuo. The residue was diluted with ethyl acetate (100 ml), washed with a saturated potassium carbonate aqueous solution, dried over magnesium sulfate and evaporated in vacuo. The residue was purified by column chromatography on silica gel with a mixture of dichloromethane and hexane (1:1) as eluent. The fractions containing the object product were collected and evaporated in vacuo to afford 5-ethoxycarbonyl-3-(4-nitrophenyl)-1,2,4-oxadiazole.

Quelle