Реакция #1005949

Уравнение реакции

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

thionyl chloride

→

title compound

Выход 86.0%

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

Выход 86.0%

Растворители

1,2-dichloroethane

Условия реакции

Обработка

1. 1
   Температураthe mixture was refluxed
2. 2
   Температураunder heating for 5 hours
3. 3
   ДругоеAfter removing the solvent
4. 4
   Другоеby 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
   Температураthe solution was refluxed
9. 9
   Температураunder heating for one hour
10. 10
    ТемператураAfter cooling
11. 11
    workup.ADDITIONthe reaction solution was poured over ice water
12. 12
    Экстракцияextracted with ethyl acetate
13. 13
    ТемператураAfter cooling
14. 14
    Экстракцияthe extraction
15. 15
    workup.ADDITIONby adding water and ethyl acetate to the solution
16. 16
    СушкаThe organic layer was dried over magnesium sulfate
17. 17
    ДругоеThe solvent was evaporated off under reduced pressure
18. 18
    Другоеthe residue was then purified by a silica gel chromatography

Методика

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%).

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