반응 #161947

반응 방정식

Sodium

ethyl 2-(acetylamino)-2-cyanoacetate

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

→

#99

수율 95.2%

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

수율 95.2%

용매

ethanol

반응 조건

후처리

1. 1
   온도the reaction mixture was heated
2. 2
   온도at reflux overnight
3. 3
   여과filtered
4. 4
   농축concentrated in vacuo
5. 5
   workup.ADDITIONThe residue was diluted with water
6. 6
   추출extracted with ethyl acetate
7. 7
   세척The organic layer was washed with brine
8. 8
   건조dried over sodium sulfate
9. 9
   여과filtered
10. 10
    농축concentrated in vacuo
11. 11
    기타to give a dark oil, which
12. 12
    기타was purified by silica gel chromatography (Gradient: 0% to 50% ethyl acetate in heptane)

실험 절차

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.

출처