Hydrochloric Acid → 4-{[4-(3-Chloropropoxy)-2-methylphenyl]methyl}-5-isopropyl-3-(2,3,4,6-tetra-O-pivaloyl-beta-D-glucopyranosyloxy)-1H-pyrazole

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Reaction Steps

To a solution of 4-[(4-hydroxy-2-methylphenyl)methyl]-5-isopropyl-3-(2,3,4,6-tetra-O-pivaloyl-β-D-glucopyranosyloxy)-1H-pyrazole (8.58 g), 1-bromo-3-chloropropane (2.85 mL) and tetra(n-butyl)ammonium bromide (1.86 g) in tetrahydrofuran (43 mL) was added 5 mol/L aqueous sodium hydroxide solution (5.76 mL), and the mixture was stirred at room temperature overnight. The reaction mixture was poured into 1 mol/L hydrochloric acid, and the resulting mixture was extracted with diethyl ether. The extract was washed with 1 mol/L hydrochloric acid, water and brine successively, and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure, and the residue was dissolved in n-hexane (15 mL)-diisopropyl ether (5 mL) under reflux condition. The solution was cooled to room temperature, and n-hexane (25 mL) was added to the solution. The precipitated crystals were collected by filtration, and the crystals were washed with n-hexane and dried under reduced pressure to give the title compound (6.06 g).

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