반응 #50562

반응 방정식

ethyl indole-2-carboxylate

sodium hydride

ethyl acrylate

sodium hydride

Ethyl acrylate

→

2,3-dihydro-1-oxo-2-ethoxycarbonyl-1H-pyrrolo[1,2-a]indole

용매

toluene

반응 조건

후처리

1. 1
   온도the mixture was heated
2. 2
   온도at reflux
3. 3
   기타After a total time of 6 hr, t.l.c
4. 4
   기타are consumed
5. 5
   기타The mixture was quenched with ethanol
6. 6
   workup.ADDITIONtreated with water, dilute HCl, and methylene chloride
7. 7
   세척The organic phase was washed with brine
8. 8
   건조dried over sodium sulfate
9. 9
   여과filtered
10. 10
    농축concentrated

실험 절차

A stirred solution of ethyl indole-2-carboxylate (5.67 g, 30 mmol) in 400 ml of toluene under N was treated with sodium hydride (1.44 g, 36 mmol). Ethyl acrylate (3.6 ml, 33 mol) was added and the mixture was heated at reflux. Additional portions of ethyl acrylate (6 mmol) and sodium hydride (16 mmol) were added after 3 hr. After a total time of 6 hr, t.l.c. indicated that all starting material are consumed. The mixture was quenched with ethanol and treated with water, dilute HCl, and methylene chloride. The organic phase was washed with brine, dried over sodium sulfate, filtered, and concentrated to give 2,3-dihydro-1-oxo-2-ethoxycarbonyl-1H-pyrrolo[1,2-a]indole, which was used directly in the next step.

출처