反応 #1552025

反応方程式

Toluene

p-toluenesulfonic acid monohydrate

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

→

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

収率 91.2%

溶媒

water

反応条件

後処理

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

実験手順

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.

出典