Reaktion #161947

Reaktionsgleichung

Sodium

ethyl 2-(acetylamino)-2-cyanoacetate

7-bromobicyclo[4.2.0]octa-1,3,5-triene

→

#99

Ausbeute 95.2%

ethyl (acetylamino)(bicyclo[4.2.0]octa-1,3,5-trien-7-yl)cyanoacetate

Ausbeute 95.2%

Lösungsmittel

ethanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturthe reaction mixture was heated
2. 2
   Temperaturat reflux overnight
3. 3
   Filtrationfiltered
4. 4
   Einengenconcentrated in vacuo
5. 5
   workup.ADDITIONThe residue was diluted with water
6. 6
   Extraktionextracted with ethyl acetate
7. 7
   WaschenThe organic layer was washed with brine
8. 8
   Trocknendried over sodium sulfate
9. 9
   Filtrationfiltered
10. 10
    Einengenconcentrated in vacuo
11. 11
    Sonstigeto give a dark oil, which
12. 12
    Sonstigewas purified by silica gel chromatography (Gradient: 0% to 50% ethyl acetate in heptane)

Vorschrift

Sodium (464 mg, 20.2 mmol, 1.2 eq.) was allowed to react with absolute ethanol (40 mL, 0.42 M); to the resulting mixture was added ethyl 2-(acetylamino)-2-cyanoacetate (3.44 g, 20.2 mmol, 1.2 eq.). After 20 minutes at 60° C., 7-bromobicyclo[4.2.0]octa-1,3,5-triene (3.092 g, 16.89 mmol, 1 eq.) was added and the reaction mixture was heated at reflux overnight, then filtered and concentrated in vacuo. The residue was diluted with water and extracted with ethyl acetate. The organic layer was washed with brine, dried over sodium sulfate, filtered, and concentrated in vacuo to give a dark oil, which was purified by silica gel chromatography (Gradient: 0% to 50% ethyl acetate in heptane) to give #99 (4.38 g) as a yellow gum. LC-MS: m/z 273.2 [M+H+], retention time=2.36 minutes.

Quelle