Reaction #1914830

Reaction equation

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

Yield 46.6%

Solvents

acetonitrile

Conditions

Workup

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

Procedure

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