Hydrochloric Acid → HCID 86605886, compound

Participants

Reaction Conditions

Reaction Steps

To a mixture of methyl 5-{4-[(4-{[(4-formyl-1-phenyl-1H-pyrazol-3-yl)oxy]methyl}2-methoxyphenoxy)methyl]-5-methyl-1,3-oxazol-2-yl}-2-(methanesulfonyloxy)benzoate (0.50 g), tetrahydrofuran (3 mL) and ethanol (3 mL) was added 1N aqueous sodium hydroxide solution (3 mL), and the mixture was stirred at 50° C. for 1 hr. To the reaction mixture were added 1N hydrochloric acid (3 mL) and water, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated to give pale-yellow crystal. A mixture of the crystal, potassium carbonate (0.21 g), methyl iodide (0.55 g) and N,N-dimethylformamide (10 mL) was stirred at room temperature for 3 hrs. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated to give methyl 5-{4-[(4-{[(4-formyl-1-phenyl-1H-pyrazol-3-yl)oxy]methyl}2-methoxyphenoxy)methyl]-5-methyl-1,3-oxazol-2-yl}-2-methoxybenzoate as pale-yellow crystals (0.30 g, yield 67%). Recrystallization from ethyl acetate-hexane gave colorless prism crystals. melting point: 165-166° C.

Provenance & Evidence