تفاعل #4015

معادلة التفاعل

ethyl 2-chloroacetoacetate

ethacrolein

ammonium acetate

→

title product

المردود 43.2%

ethyl 5-ethyl-2-methylnicotinate

المردود 43.2%

المذيبات

acetonitrile

acetonitrile

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةThe reaction mixture is heated
2. 2
   درجة الحرارةat reflux for 16 hours
3. 3
   درجة الحرارةcooled
4. 4
   أخرىpartitioned between water and ethyl acetate
5. 5
   تركيزThe organic phase is concentrated in vacuo
6. 6
   أخرىchromatographed on silica gel using 9:1 hexane-ethylacetate

الإجراء التجريبي

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.

المصدر