反応 #50564

反応方程式

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

溶媒

toluene

反応条件

後処理

1. 1
   温度The mixture was heated to reflux
2. 2
   その他After a total of 8 hr, the starting material was consumed completely
3. 3
   その他the mixture was quenched with ethanol
4. 4
   workup.ADDITIONtreated with water and dilute HCl and methylene chloride
5. 5
   洗浄The organic layer was washed with brine
6. 6
   その他dried
7. 7
   濃縮concentrated

実験手順

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.

出典