Реакция #61393

Уравнение реакции

Water

1,2-dihydro-4-[(4-methylthiophenyl)-methyl]-5-trifluoromethyl-3H-pyrazol-3-one

acetobromo-α-D-glucose

potassium carbonate

→

4-[(4-methylthiophenyl)methyl]-3-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)-5-trifluoromethyl-1H-pyrazole

Выход 46.6%

Растворители

acetonitrile

Условия реакции

Обработка

1. 1
   Экстракцияthe resulting mixture was extracted with ethyl acetate
2. 2
   ПромывкаThe organic layer was washed with a saturated aqueous sodium hydrogen carbonate solution and brine
3. 3
   Сушкаdried over anhydrous magnesium sulfate
4. 4
   ДругоеThe solvent was removed under reduced pressure
5. 5
   Другоеthe residue was purified by column chromatography on silica gel (eluent: hexane/ethyl acetate=1/1)

Методика

To a solution of 1,2-dihydro-4-[(4-methylthiophenyl)-methyl]-5-trifluoromethyl-3H-pyrazol-3-one (2.0 g) in acetonitrile (100 mL) were added acetobromo-α-D-glucose (3.1 g) and potassium carbonate (1.1 g), and the mixture was stirred at room temperature overnight. Water was added to the reaction mixture, and the resulting mixture was extracted with ethyl acetate. The organic layer was washed with a saturated aqueous sodium hydrogen carbonate solution and brine and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure, and the residue was purified by column chromatography on silica gel (eluent: hexane/ethyl acetate=1/1) to give 4-[(4-methylthiophenyl)methyl]-3-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)-5-trifluoromethyl-1H-pyrazole (2.0 g).

Источник