تفاعل #1005949

معادلة التفاعل

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

thionyl chloride

→

title compound

المردود 86.0%

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

المردود 86.0%

المذيبات

1,2-dichloroethane

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةthe mixture was refluxed
2. 2
   درجة الحرارةunder heating for 5 hours
3. 3
   أخرىAfter removing the solvent
4. 4
   أخرىby 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
   درجة الحرارةthe solution was refluxed
9. 9
   درجة الحرارةunder heating for one hour
10. 10
    درجة الحرارةAfter cooling
11. 11
    workup.ADDITIONthe reaction solution was poured over ice water
12. 12
    استخلاصextracted with ethyl acetate
13. 13
    درجة الحرارةAfter cooling
14. 14
    استخلاصthe extraction
15. 15
    workup.ADDITIONby adding water and ethyl acetate to the solution
16. 16
    تجفيفThe organic layer was dried over magnesium sulfate
17. 17
    أخرىThe solvent was evaporated off under reduced pressure
18. 18
    أخرىthe residue was then purified by a silica gel chromatography

الإجراء التجريبي

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%).

المصدر