Reacción #1182439

Ecuación de reacción

bromoethane

4′-(2,3-Difluoro-4-(4-pentylcylohexyl)phenyl)bi(cyclohexane)-4-ol

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

sodium hydride

water

→

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

Disolventes

dimethylformamide

dimethylformamide

toluene

Condiciones de reacción

Tratamiento posterior

1. 1
   Otrowere put in a reaction vessel under a nitrogen atmosphere
2. 2
   workup.ADDITIONwas added dropwise
3. 3
   Temperaturathe mixture was heated to 120° C
4. 4
   workup.WAITThe stirring was continued for 2 hours
5. 5
   Temperaturacooled slowly to room temperature
6. 6
   workup.ADDITIONmixed
7. 7
   Otrohad separated into two phases
8. 8
   Lavadowashed sequentially with water
9. 9
   Secadoa saturated aqueous solution of sodium hydrogencarbonate and brine, and then dried over anhydrous magnesium sulfate
10. 10
    ConcentraciónThe solution was concentrated under reduced pressure
11. 11
    Otrothe residue was purified with a fractional operation by means of column chromatography
12. 12
    Otrosilica gel as a stationary phase powder, and further purified by means of recrystallization from a mixed solvent of heptane and Solmix (heptane: Solmix=1:1 by volume)
13. 13
    Otrodried

Procedimiento

4′-(2,3-Difluoro-4-(4-pentylcylohexyl)phenyl)bi(cyclohexane)-4-ol (48) (5.0 g) synthesized according to the method described in Example 7, sodium hydride (0.59 g) and dimethylformamide (50 ml) were put in a reaction vessel under a nitrogen atmosphere, and heated to 60° C. The mixture was stirred for 1 hour, then bromoethane (49) (1.34 g) dissolved in dimethylformamide (10 ml) was added dropwise thereto, and the mixture was heated to 120° C. The stirring was continued for 2 hours, and cooled slowly to room temperature, and then water (200 ml) and toluene (200 ml) were added and mixed thereto. The mixture was then 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 water and a saturated aqueous solution of sodium hydrogencarbonate and brine, 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 heptane (toluene:heptane=2:1 by volume) as an eluent and silica gel as a stationary phase powder, and further purified by means of recrystallization from a mixed solvent of heptane and Solmix (heptane: Solmix=1:1 by volume), and dried, giving 3.2 g of 4-(2,3-difluoro-4-(4-pentylcyclohexyl)phenyl-4′-ethoxybi(cyclohexane) (No. 168). The yield based on the compound (48) was 59.5%.

Fuente