Reacción #836005

Ecuación de reacción

cyanomethylenetri-n-butylphosphorane

2-[(4-chlorophenyl)sulfonylmethyl]-1,4-difluorobenzene

tetrahydrothiopyran-4-ol

cyanomethylenetri-n-butylphosphorane

→

title compound

Rendimiento 61.0%

4-[[(4-Chlorophenyl)sulfonyl](2,5-difluorophenyl)methyl]tetrahydrothiopyran

Rendimiento 61.0%

Disolventes

toluene

hexane diisopropyl ether

Condiciones de reacción

Tratamiento posterior

1. 1
   TemperaturaUnder an argon atmosphere, the resulting mixture was heated
2. 2
   Temperaturaunder reflux for 14 hours
3. 3
   Temperaturato cool down
4. 4
   TemperaturaUnder an argon atmosphere, the resulting mixture was heated
5. 5
   Temperaturaunder reflux for 14 hours
6. 6
   Temperaturato cool down
7. 7
   OtroThe residue obtained
8. 8
   Concentraciónby concentrating the reaction mixture under reduced pressure
9. 9
   Otrothe fraction obtained from the hexane
10. 10
    Concentraciónethyl acetate=15:1 eluate was concentrated under reduced pressure
11. 11
    Otroto give a white solid

Procedimiento

The 2-[(4-chlorophenyl)sulfonylmethyl]-1,4-difluorobenzene (500 mg, 1.65 mmol) obtained in Example 5 and tetrahydrothiopyran-4-ol (400 mg, 3.38 mmol) were dissolved in toluene (20 ml), followed by the addition of cyanomethylenetri-n-butylphosphorane (800 mg, 3.31 mmol). Under an argon atmosphere, the resulting mixture was heated under reflux for 14 hours. After the reaction mixture was allowed to cool down, cyanomethylenetri-n-butylphosphorane (400 mg, 1.66 mmol) was added. Under an argon atmosphere, the resulting mixture was heated under reflux for 14 hours. The reaction mixture was then allowed to cool down. The residue obtained by concentrating the reaction mixture under reduced pressure was subjected to flash silica gel chromatography, and the fraction obtained from the hexane:ethyl acetate=15:1 eluate was concentrated under reduced pressure to give a white solid. The white solid was washed with a hexane/diisopropyl ether mixture, whereby the title compound (404 mg, 1.00 mmol, 61%) was obtained as a white powder.

Fuente