تفاعل #980609

معادلة التفاعل

ethyl isobutyrylacetate

pyridine-2-carboxaldehyde

→

title compound

المردود 83.6%

4-Methyl-3-oxo-2-(2-pyridinylmethylene)-pentanoic acid, ethyl ester

المردود 83.6%

المذيبات

benzene

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةat reflux for 3 hours
2. 2
   غسيلthe cooled mixture was washed with water, saturated NaHCO3 and saturated NaCl solutions
3. 3
   تجفيفdried (Na2SO4) ) and
4. 4
   تركيزconcentrated in vacuo
5. 5
   أخرىThe crude product was purified by flash chromatography on silica gel eluting with ethyl acetate (EtOAc)-hexane (1:9)

الإجراء التجريبي

To a solution of ethyl isobutyrylacetate (15.78 g, 99.7 mmol) and pyridine-2-carboxaldehyde (10.7 g, 99.9 mmol) in dry benzene (100 mL) at room temperature under argon was added acetic acid (0.30 mL, 5.2 mmol) and piperidine (0.80 mL, 8.1 mmol). After stirring at room tempertaure for 1 hour and at reflux for 3 hours, the cooled mixture was washed with water, saturated NaHCO3 and saturated NaCl solutions, dried (Na2SO4) ) and concentrated in vacuo. The crude product was purified by flash chromatography on silica gel eluting with ethyl acetate (EtOAc)-hexane (1:9) to give title compound (20.61 g, 83%) as an orange, viscous oil which crystallized on standing to a semi-solid mass, mp 53°-55° C.

المصدر