반응 #1552025

반응 방정식

Toluene

p-toluenesulfonic acid monohydrate

3-butyl-1-(4-ethoxy-2,3-difluorophenyl)cyclopentanol

→

1-(3-butylcyclopent-1-enyl)-4-ethoxy-2,3-difluorobenzene

수율 91.2%

용매

water

반응 조건

후처리

1. 1
   기타obtained in the second step, in a reaction vessel
2. 2
   기타equipped with a Dean-Stark apparatus under an atmosphere of nitrogen
3. 3
   온도The mixture was refluxed for 30 minutes
4. 4
   기타was removed with a Dean-Stark apparatus
5. 5
   세척was washed with water
6. 6
   건조The solution was dried over anhydrous magnesium sulfate
7. 7
   workup.DISTILLATIONthe solvent was distilled off under reduced pressure
8. 8
   기타The residue was purified by silica gel chromatography (eluent: ethyl acetate/n-heptane=1/9 by volume)

실험 절차

Toluene (50 ml) and p-toluenesulfonic acid monohydrate (0.14 g) were added to 3-butyl-1-(4-ethoxy-2,3-difluorophenyl)cyclopentanol (2.8 g) obtained in the second step, in a reaction vessel equipped with a Dean-Stark apparatus under an atmosphere of nitrogen. The mixture was refluxed for 30 minutes, while forming water was removed with a Dean-Stark apparatus. The reaction solution was cooled to room temperature and was washed with water. The solution was dried over anhydrous magnesium sulfate and the solvent was distilled off under reduced pressure. The residue was purified by silica gel chromatography (eluent: ethyl acetate/n-heptane=1/9 by volume) to give a mixture (2.4 g) of 1-(3-butylcyclopent-1-enyl)-4-ethoxy-2,3-difluorobenzene and 1-(4-butylcyclopent-1-enyl)-4-ethoxy-2,3-difluorobenzene.

출처