Reaktion #4015

Reaktionsgleichung

ethyl 2-chloroacetoacetate

ethacrolein

ammonium acetate

→

title product

Ausbeute 43.2%

ethyl 5-ethyl-2-methylnicotinate

Ausbeute 43.2%

Lösungsmittel

acetonitrile

acetonitrile

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe reaction mixture is heated
2. 2
   Temperaturat reflux for 16 hours
3. 3
   Temperaturcooled
4. 4
   Sonstigepartitioned between water and ethyl acetate
5. 5
   EinengenThe organic phase is concentrated in vacuo
6. 6
   Sonstigechromatographed on silica gel using 9:1 hexane-ethylacetate

Vorschrift

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.

Quelle