반응 #4014

반응 방정식

ethacrolein

diethyl 3-chloro-2-oxo-butanedioate

ammonium sulfamate

→

title product

수율 86.0%

diethyl 5-ethylpyridine-2,3-dicarboxylate

수율 86.0%

용매

ethanol

반응 조건

후처리

1. 1
   온도is heated
2. 2
   온도at reflux
3. 3
   기타the solvent removed by distillation under reduced pressure
4. 4
   workup.ADDITIONThe residue is treated with water
5. 5
   추출extracted with ethyl acetate
6. 6
   기타The organic phase is separated
7. 7
   농축concentrated in vacuo
8. 8
   기타the residue purified by column chromatography on silica gel using 4:1 hexane-ethyl acetate as the eluent

실험 절차

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.

출처