反应 #1005949

反应方程式

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

thionyl chloride

→

title compound

收率 86.0%

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

收率 86.0%

溶剂

1,2-dichloroethane

反应条件

后处理

1. 1
   温度the mixture was refluxed
2. 2
   温度under heating for 5 hours
3. 3
   其他After removing the solvent
4. 4
   其他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
    萃取extracted with ethyl acetate
13. 13
    温度After cooling
14. 14
    萃取the extraction
15. 15
    workup.ADDITIONby adding water and ethyl acetate to the solution
16. 16
    干燥The organic layer was dried over magnesium sulfate
17. 17
    其他The solvent was evaporated off under reduced pressure
18. 18
    其他the residue was then purified by a silica gel chromatography

实验过程

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%).

来源