Реакция #2446064

Уравнение реакции

Toluene

p-toluenesulfonic acid monohydrate

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

→

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

Выход 91.2%

Растворители

water

Условия реакции

Обработка

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

Методика

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.

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