反応 #4014

反応方程式

ethacrolein

diethyl 3-chloro-2-oxo-butanedioate

ammonium sulfamate

→

title product

収率 86.0%

diethyl 5-ethylpyridine-2,3-dicarboxylate

収率 86.0%

溶媒

ethanol

反応条件

後処理

1. 1
   温度is heated
2. 2
   温度at reflux
3. 3
   その他the solvent removed by distillation under reduced pressure
4. 4
   workup.ADDITIONThe residue is treated with water
5. 5
   抽出extracted with ethyl acetate
6. 6
   その他The organic phase is separated
7. 7
   濃縮concentrated in vacuo
8. 8
   その他the residue purified by column chromatography on silica gel using 4:1 hexane-ethyl acetate as the eluent

実験手順

A stirred mixture of ethacrolein, (4.2 g, 0.05 mol), diethyl 3-chloro-2-oxo-butanedioate, (11.2 g, 0.05 mol) and ammonium sulfamate, (15.4 g, 0.135 mol) in ethanol (37 mL) is heated at reflux. After 15 hours the mixture is cooled to room temperature and the solvent removed by distillation under reduced pressure. The residue is treated with water and extracted with ethyl acetate. The organic phase is separated and concentrated in vacuo and the residue purified by column chromatography on silica gel using 4:1 hexane-ethyl acetate as the eluent to give 10.8 g (75% yield) of the title product as an oil which is shown to be 95% pure by a gas chromatography assay.

出典