Reacción #1182437

Ecuación de reacción

compound ( 46 )

8-(4-(2,3-difluoro-4-(4-pentylcyclohexyl)phenyl)cyclohexyl)-1,4-dioxaspiro[4,5]decane

formic acid

Water

→

4′-(2,3-difluoro-4-(4-pentylcyclohexyl)phenyl)bi(cyclohexane)-4-one

Rendimiento 45.8%

Disolventes

toluene

toluene

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturaheated
2. 2
   Temperaturaunder reflux for 3 hours
3. 3
   workup.ADDITIONmixed
4. 4
   Otrohad separated into two phases
5. 5
   Lavadowashed sequentially with a saturated aqueous solution of sodium hydrogencarbonate and water
6. 6
   Secadodried over anhydrous magnesium sulfate
7. 7
   ConcentraciónThe solution was concentrated under reduced pressure
8. 8
   Otrothe residue was purified with a fractional operation by means of column chromatography
9. 9
   OtroThe residue was further purified by means of recrystallization from a mixed solvent of toluene and heptane (toluene: heptane=1:1 by volume)
10. 10
    Otrodried

Procedimiento

The compound (46) (36.7 g), formic acid (120 g) and toluene (120 ml) were put in a reaction vessel under a nitrogen atmosphere, heated under reflux for 3 hours, and cooled slowly to room temperature. Water (300 ml) and toluene (300 ml) were added and mixed thereto. The mixture was allowed to stand until it had separated into two phases, the organic and aqueous phases, and an extractive operation to an organic phase was carried out. The organic phase was fractionated, and washed sequentially with a saturated aqueous solution of sodium hydrogencarbonate and water, and then dried over anhydrous magnesium sulfate. The solution was concentrated under reduced pressure, and the residue was purified with a fractional operation by means of column chromatography using a mixed solvent of toluene and ethyl acetate (toluene:ethyl acetate=9:1 by volume) as an eluent and silica gel as a stationary phase powder. The residue was further purified by means of recrystallization from a mixed solvent of toluene and heptane (toluene: heptane=1:1 by volume), and dried, giving 15.3 g of 4′-(2,3-difluoro-4-(4-pentylcyclohexyl)phenyl)bi(cyclohexane)-4-one (47). The yield based on the compound (46) was 45.9%.

Fuente