Réaction #2446064

Équation de réaction

Toluene

p-toluenesulfonic acid monohydrate

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

→

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

Rendement 91.2%

Solvants

water

Conditions de réaction

Traitement

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

Mode opératoire

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.

Source