Réaction #61393

Équation de réaction

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

Rendement 46.6%

Solvants

acetonitrile

Conditions de réaction

Traitement

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

Mode opératoire

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).

Source