تفاعل #161947

معادلة التفاعل

Sodium

ethyl 2-(acetylamino)-2-cyanoacetate

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

→

#99

المردود 95.2%

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

المردود 95.2%

المذيبات

ethanol

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةthe reaction mixture was heated
2. 2
   درجة الحرارةat reflux overnight
3. 3
   ترشيحfiltered
4. 4
   تركيزconcentrated in vacuo
5. 5
   workup.ADDITIONThe residue was diluted with water
6. 6
   استخلاصextracted with ethyl acetate
7. 7
   غسيلThe organic layer was washed with brine
8. 8
   تجفيفdried over sodium sulfate
9. 9
   ترشيحfiltered
10. 10
    تركيزconcentrated in vacuo
11. 11
    أخرىto give a dark oil, which
12. 12
    أخرىwas purified by silica gel chromatography (Gradient: 0% to 50% ethyl acetate in heptane)

الإجراء التجريبي

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.

المصدر