반응 #1148625

반응 방정식

2-(4-chloro-3-methoxy-2-pyridyl)-2-cyclopropylethanal

piperidine

acetic acid

diethylmalonate

→

ethyl 8-chloro-1-cyclopropyl-9-methoxy-4-oxo-4H-quinolizine-3-carboxylate

ethyl 8-chloro-1-cyclopropyl-9-methyl-4-oxo-4H-quinolizine-3-carboxylate

용매

ethanol

반응 조건

후처리

1. 1
   workup.DISTILLATIONThe solvent was distilled off under reduced pressure
2. 2
   workup.ADDITIONthe resulting mixture was diluted with ether
3. 3
   세척the resulting organic layer was washed with water and saturated salt water
4. 4
   건조dried over anhydrous sodium sulfate
5. 5
   workup.DISTILLATIONthe solvent was distilled off under reduced pressure
6. 6
   workup.ADDITION20 ml of Dowtherm A was added to the resulting residue
7. 7
   온도the resulting mixture was heated at 240° C. for 30 minutes
8. 8
   기타The reaction solution was purified directly by silica gel column chromatography (eluent; hexane→hexane:ethyl acetate=1:1)

실험 절차

0.85 g of 2-(4-chloro-3-methoxy-2-pyridyl)-2-cyclopropylethanal (XII) was dissolved in 27 ml of anhydrous ethanol, and 0.89 ml of piperidine, 0.89 ml of acetic acid and 2.85 ml of diethylmalonate were added thereto and the resulting mixture was heated at 100° C. for 5.5 hours. The solvent was distilled off under reduced pressure, and thereafter, the resulting mixture was diluted with ether and the resulting organic layer was washed with water and saturated salt water, and thereafter, dried over anhydrous sodium sulfate and the solvent was distilled off under reduced pressure. 20 ml of Dowtherm A was added to the resulting residue and the resulting mixture was heated at 240° C. for 30 minutes. The reaction solution was purified directly by silica gel column chromatography (eluent; hexane→hexane:ethyl acetate=1:1) to obtain 0.67 g of ethyl 8-chloro-1-cyclopropyl-9-methoxy-4-oxo-4H-quinolizine-3-carboxylate (XIII).

출처