Reacción #2446064

Ecuación de reacción

Toluene

p-toluenesulfonic acid monohydrate

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

→

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

Rendimiento 91.2%

Disolventes

water

Condiciones de reacción

Tratamiento posterior

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

Procedimiento

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.

Fuente