반응 #1005949

반응 방정식

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

thionyl chloride

→

title compound

수율 86.0%

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

수율 86.0%

용매

1,2-dichloroethane

반응 조건

후처리

1. 1
   온도the mixture was refluxed
2. 2
   온도under heating for 5 hours
3. 3
   기타After removing the solvent
4. 4
   기타by 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
   온도the solution was refluxed
9. 9
   온도under heating for one hour
10. 10
    온도After cooling
11. 11
    workup.ADDITIONthe reaction solution was poured over ice water
12. 12
    추출extracted with ethyl acetate
13. 13
    온도After cooling
14. 14
    추출the extraction
15. 15
    workup.ADDITIONby adding water and ethyl acetate to the solution
16. 16
    건조The organic layer was dried over magnesium sulfate
17. 17
    기타The solvent was evaporated off under reduced pressure
18. 18
    기타the residue was then purified by a silica gel chromatography

실험 절차

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%).

출처