반응 #50564

반응 방정식

ethyl 5-methoxy-indole-2-carboxylate

sodium hydride

ethylacrylate

ethyl acrylate

sodium hydride

→

2,3-dihydro-1-oxo-7-methoxy-2-ethoxycarbonyl-1H-pyrrolo[1,2-a]indole

용매

toluene

반응 조건

후처리

1. 1
   온도The mixture was heated to reflux
2. 2
   기타After a total of 8 hr, the starting material was consumed completely
3. 3
   기타the mixture was quenched with ethanol
4. 4
   workup.ADDITIONtreated with water and dilute HCl and methylene chloride
5. 5
   세척The organic layer was washed with brine
6. 6
   기타dried
7. 7
   농축concentrated

실험 절차

A stirred solution of ethyl 5-methoxy-indole-2-carboxylate (30 g, 137 mmol) in 1.5 L of toluene under N2 was treated with sodium hydride (6.7 g of 60% in oil, 167 mmol) and ethylacrylate (16.3 ml, 150 mmol). The mixture was heated to reflux. After 3 hours (hr), additional ethyl acrylate (3 ml) and sodium hydride (3.3 g) were added. After a total of 8 hr, the starting material was consumed completely and the mixture was quenched with ethanol and treated with water and dilute HCl and methylene chloride. The organic layer was washed with brine, dried and concentrated to give 2,3-dihydro-1-oxo-7-methoxy-2-ethoxycarbonyl-1H-pyrrolo[1,2-a]indole, which was used directly in the next step.

출처