反応 #4015

反応方程式

ethyl 2-chloroacetoacetate

ethacrolein

ammonium acetate

→

title product

収率 43.2%

ethyl 5-ethyl-2-methylnicotinate

収率 43.2%

溶媒

acetonitrile

acetonitrile

反応条件

後処理

1. 1
   温度The reaction mixture is heated
2. 2
   温度at reflux for 16 hours
3. 3
   温度cooled
4. 4
   その他partitioned between water and ethyl acetate
5. 5
   濃縮The organic phase is concentrated in vacuo
6. 6
   その他chromatographed on silica gel using 9:1 hexane-ethylacetate

実験手順

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.

出典