Reacción #4015

Ecuación de reacción

ethyl 2-chloroacetoacetate

ethacrolein

ammonium acetate

→

title product

Rendimiento 43.2%

ethyl 5-ethyl-2-methylnicotinate

Rendimiento 43.2%

Disolventes

acetonitrile

acetonitrile

Condiciones de reacción

Tratamiento posterior

1. 1
   TemperaturaThe reaction mixture is heated
2. 2
   Temperaturaat reflux for 16 hours
3. 3
   Temperaturacooled
4. 4
   Otropartitioned between water and ethyl acetate
5. 5
   ConcentraciónThe organic phase is concentrated in vacuo
6. 6
   Otrochromatographed on silica gel using 9:1 hexane-ethylacetate

Procedimiento

A mixture of ethacrolein (12.8 g 0.152 mole) and ammonium acetate (24.4 g 0.304 mole) in 50 cc acetonitrile is stirred at room temperature and a solution of ethyl 2-chloroacetoacetate (25 g 0.152 mole) in 30 cc acetonitrile is added dropwise over 15 minutes. The reaction mixture is heated at reflux for 16 hours, cooled, and partitioned between water and ethyl acetate. The organic phase is concentrated in vacuo and chromatographed on silica gel using 9:1 hexane-ethylacetate to afford 12.7 g of the title product.

Fuente