Reacción #1755494

Ecuación de reacción

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

Rendimiento 46.6%

Disolventes

acetonitrile

Condiciones de reacción

Tratamiento posterior

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

Procedimiento

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).

Fuente