Реакция #2254163

Уравнение реакции

2,2,2-trifluoroethyl trifluoromethanesulfonate

3-amino-2,3-bis(hydroxyimino)propionitrile

2,2,2-trifluoroethyl trifluoromethanesulfonate

sodium hydride

potassium carbonate

→

title compound

Выход 132.6%

3-amino-2,3-bis(2,2,2-trifluoroethoxyimino)propionitrile

Выход 132.6%

Растворители

water

N,N-dimethylformamide

Условия реакции

Обработка

1. 1
   ТемператураThe mixture was cooled to 0° C
2. 2
   workup.STIRRINGStirring
3. 3
   workup.WAITwas conducted at room temperature for 2 hours
4. 4
   ЭкстракцияExtraction with ethyl acetate
5. 5
   ДругоеThe organic layer obtained
6. 6
   Промывкаwas washed with a saturated aqueous sodium chloride solution
7. 7
   Сушкаdried over anhydrous magnesium sulfonate
8. 8
   Фильтрацияfiltered
9. 9
   Другоеto remove inorganic matter
10. 10
    workup.DISTILLATIONThe solvent was distilled off under reduced pressure
11. 11
    ДругоеThe resulting residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:2)

Методика

1.81 g (7.81 mM) of 2,2,2-trifluoroethyl trifluoromethanesulfonate was added to an N,N-dimethylformamide solution (20 ml) of 1.00 g (7.81 mM) of 3-amino-2,3-bis(hydroxyimino)propionitrile. The mixture was cooled to 0° C. Thereto was added 1.08 g (7.81 M) of potassium carbonate. Stirring was conducted at room temperature for 3 hours. The mixture was cooled to 0° C. Thereto were added 1.81 g (7.81 mM) of 2,2,2-trifluoroethyl trifluoromethanesulfonate and 0.34 g (7.8 mM) of 55% sodium hydride. Stirring was conducted at room temperature for 2 hours. The reaction mixture was poured into water. Extraction with ethyl acetate was conducted. The organic layer obtained was washed with a saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfonate, and filtered to remove inorganic matter. The solvent was distilled off under reduced pressure. The resulting residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:2) to obtain 1.51 g (yield: 66%) of the title compound.

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