Réaction #1005949

Équation de réaction

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

thionyl chloride

→

title compound

Rendement 86.0%

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

Rendement 86.0%

Solvants

1,2-dichloroethane

Conditions de réaction

Traitement

1. 1
   Températurethe mixture was refluxed
2. 2
   Températureunder heating for 5 hours
3. 3
   AutreAfter removing the solvent
4. 4
   Autreby 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
   Températurethe solution was refluxed
9. 9
   Températureunder heating for one hour
10. 10
    TempératureAfter cooling
11. 11
    workup.ADDITIONthe reaction solution was poured over ice water
12. 12
    Extractionextracted with ethyl acetate
13. 13
    TempératureAfter cooling
14. 14
    Extractionthe extraction
15. 15
    workup.ADDITIONby adding water and ethyl acetate to the solution
16. 16
    SéchageThe organic layer was dried over magnesium sulfate
17. 17
    AutreThe solvent was evaporated off under reduced pressure
18. 18
    Autrethe residue was then purified by a silica gel chromatography

Mode opératoire

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%).

Source