Réaction #4015

Équation de réaction

ethyl 2-chloroacetoacetate

ethacrolein

ammonium acetate

→

title product

Rendement 43.2%

ethyl 5-ethyl-2-methylnicotinate

Rendement 43.2%

Solvants

acetonitrile

acetonitrile

Conditions de réaction

Traitement

1. 1
   TempératureThe reaction mixture is heated
2. 2
   Températureat reflux for 16 hours
3. 3
   Températurecooled
4. 4
   Autrepartitioned between water and ethyl acetate
5. 5
   ConcentrationThe organic phase is concentrated in vacuo
6. 6
   Autrechromatographed on silica gel using 9:1 hexane-ethylacetate

Mode opératoire

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.

Source