反応 #836005

反応方程式

cyanomethylenetri-n-butylphosphorane

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

tetrahydrothiopyran-4-ol

cyanomethylenetri-n-butylphosphorane

→

title compound

収率 61.0%

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

収率 61.0%

溶媒

toluene

hexane diisopropyl ether

反応条件

後処理

1. 1
   温度Under an argon atmosphere, the resulting mixture was heated
2. 2
   温度under reflux for 14 hours
3. 3
   温度to cool down
4. 4
   温度Under an argon atmosphere, the resulting mixture was heated
5. 5
   温度under reflux for 14 hours
6. 6
   温度to cool down
7. 7
   その他The residue obtained
8. 8
   濃縮by concentrating the reaction mixture under reduced pressure
9. 9
   その他the fraction obtained from the hexane
10. 10
    濃縮ethyl acetate=15:1 eluate was concentrated under reduced pressure
11. 11
    その他to give a white solid

実験手順

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.

出典