反応 #1005949

反応方程式

2-[3-(3,4,5-Trichlorophenyl)-3-(trifluoromethyl)pyrrolidin-1-yl]-4-(trifluoro-methyl)pyrimidine-5-carboxylic acid

thionyl chloride

→

title compound

収率 86.0%

{2-[3-(3,4,5-trichlorophenyl)-3-(trifluoromethyl)-pyrrolidin-1-yl]-4-(trifluoromethyl)-pyrimidin-5-yl}methanol

収率 86.0%

溶媒

1,2-dichloroethane

反応条件

後処理

1. 1
   温度the mixture was refluxed
2. 2
   温度under heating for 5 hours
3. 3
   その他After removing the solvent
4. 4
   その他by evaporation
5. 5
   workup.DISSOLUTIONthe residues were dissolved in 1,4-dioxane (20 mL)
6. 6
   workup.ADDITIONthe resulting solution was added dropwise to the mixture solution comprising water (30 mL), 1,4-dioxane (30 mL), and sodium borohydride (0.4 g) under ice cooling
7. 7
   workup.ADDITIONAfter the dropwise addition
8. 8
   温度the solution was refluxed
9. 9
   温度under heating for one hour
10. 10
    温度After cooling
11. 11
    workup.ADDITIONthe reaction solution was poured over ice water
12. 12
    抽出extracted with ethyl acetate
13. 13
    温度After cooling
14. 14
    抽出the extraction
15. 15
    workup.ADDITIONby adding water and ethyl acetate to the solution
16. 16
    乾燥The organic layer was dried over magnesium sulfate
17. 17
    その他The solvent was evaporated off under reduced pressure
18. 18
    その他the residue was then purified by a silica gel chromatography

実験手順

2-[3-(3,4,5-Trichlorophenyl)-3-(trifluoromethyl)pyrrolidin-1-yl]-4-(trifluoro-methyl)pyrimidine-5-carboxylic acid (2.0 g) was added to 1,2-dichloroethane (50 mL). To the resulting mixture, thionyl chloride (1.0 g), and one drop of N,N-dimethylformamide was added and the mixture was refluxed under heating for 5 hours. After removing the solvent by evaporation, the residues were dissolved in 1,4-dioxane (20 mL), and the resulting solution was added dropwise to the mixture solution comprising water (30 mL), 1,4-dioxane (30 mL), and sodium borohydride (0.4 g) under ice cooling. After the dropwise addition was completed, the solution was refluxed under heating for one hour. After cooling, the reaction solution was poured over ice water and then extracted with ethyl acetate. After cooling, the extraction was carried out by adding water and ethyl acetate to the solution. The organic layer was dried over magnesium sulfate. The solvent was evaporated off under reduced pressure, and the residue was then purified by a silica gel chromatography to obtain the title compound (1.65 g, 86%).

出典