反応 #50562

反応方程式

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

溶媒

toluene

反応条件

後処理

1. 1
   温度the mixture was heated
2. 2
   温度at reflux
3. 3
   その他After a total time of 6 hr, t.l.c
4. 4
   その他are consumed
5. 5
   その他The mixture was quenched with ethanol
6. 6
   workup.ADDITIONtreated with water, dilute HCl, and methylene chloride
7. 7
   洗浄The organic phase was washed with brine
8. 8
   乾燥dried over sodium sulfate
9. 9
   ろ過filtered
10. 10
    濃縮concentrated

実験手順

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.

出典