Reacción #1973900

Ecuación de reacción

compound ( 10 )

8-(4-butoxy-2,3-difluorophenyl)-1,4-dioxaspiro[4.5]decane

formic acid

water

→

1-(4-butoxy-2,3-difluorophenyl)-cyclohexan-4-one

Rendimiento 97.7%

Disolventes

toluene

toluene

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturathe mixture was heated
2. 2
   Temperaturato reflux for 2 hours
3. 3
   workup.ADDITIONmixed with it
4. 4
   Otrohad separated into two phases of organic and aqueous phases
5. 5
   Extracciónthe extraction into an organic phase
6. 6
   OtroThe resulting organic phase was separated
7. 7
   Lavadowashed successively with water
8. 8
   Secadoa saturated aqueous solution of sodium hydrogencarbonate and water, and then dried over anhydrous magnesium sulfate
9. 9
   workup.DISTILLATIONThe solvent was then distilled off under reduced pressure
10. 10
    Otrothe resulting residue was purified with a fractional operation by means of column chromatography
11. 11
    OtroThe product was further purified by recrystallization from heptane

Procedimiento

The compound (10) (47.8 g), formic acid (87%; 67.0 ml) and toluene (200 ml) were mixed, and the mixture was heated to reflux for 2 hours. After the reaction mixture had been cooled to 30° C., water (500 ml) and toluene (1,000 ml) were added to the mixture and mixed with it. The mixture was then allowed to stand until it had separated into two phases of organic and aqueous phases, and the extraction into an organic phase was carried out. The resulting organic phase was separated, and washed successively with water, a saturated aqueous solution of sodium hydrogencarbonate and water, and then dried over anhydrous magnesium sulfate. The solvent was then distilled off under reduced pressure and the resulting residue was purified with a fractional operation by means of column chromatography using silica gel as a stationary phase powder and toluene as an eluent. The product was further purified by recrystallization from heptane to give 1-(4-butoxy-2,3-difluorophenyl)-cyclohexan-4-one (11) (40.4 g). The yield based on the compound (10) was 97.8%.

Fuente