Sodium Hydroxide → 3-(2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosyloxy)-4-[(4-bromophenyl)methyl]-5-isopropyl-1H-pyrazole

Participants

Reaction Steps

To a suspension of 4-[(4-bromophenyl)methyl]-1,2-dihydro-5-isopropyl-3H-pyrazol-3-one (5.0 g) in dichloromethane (50 mL) were added acetobromo-α-D-glucose (7.0 g), benzyltri(n-butyl)ammonium chloride (5.3 g) and 5 mol/L aqueous sodium hydroxide solution (8.5 mL), and the mixture was stirred at room temperature overnight. The organic layer was separated, and the solvent was removed under reduced pressure. The residue was purified by column chromatography on silica gel (eluent: n-hexane/ethyl acetate=1/1) to give the title compound (4.12 g).

Provenance & Evidence