Réaction #7467

Équation de réaction

4-({4-[3-(benzyloxy)propyl]phenyl}methyl)-5-trifluoromethyl-1,2-dihydro-3H-pyrazole-3-one

acetobromo-α-D-glucose

potassium carbonate

→

4-({4-[3-(benzyloxy)propyl]phenyl}methyl)-5-trifluoromethyl-3-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)-1H-pyrazole

Rendement 41.8%

Solvants

acetonitrile

Conditions de réaction

Traitement

1. 1
   AutreInsoluble materials were removed by filtration
2. 2
   Autrethe solvent of the filtrate was removed under reduced pressure
3. 3
   AutreThe residue was purified by column chromatography on silica gel (eluent: hexane/ethyl acetate=1/1-1/2)

Mode opératoire

To a solution of 4-({4-[3-(benzyloxy)propyl]phenyl}methyl)-5-trifluoromethyl-1,2-dihydro-3H-pyrazole-3-one (0.83 g) and acetobromo-α-D-glucose (1.5 g) in acetonitrile (12 mL) was added potassium carbonate (0.55 g), and the mixture was stirred at 60° C. for 20 hours. Insoluble materials were removed by filtration, and the solvent of the filtrate was removed under reduced pressure. The residue was purified by column chromatography on silica gel (eluent: hexane/ethyl acetate=1/1-1/2) to give 4-({4-[3-(benzyloxy)propyl]phenyl}methyl)-5-trifluoromethyl-3-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)-1H-pyrazole (0.64 g).

Source