Hydrochloric Acid → HCID 86605885, compound

Participants

Reaction Steps

A mixture of methyl 5-{4-[(4-chloromethyl-2-methoxyphenoxy)methyl]-5-methyl-1,3-oxazol-2-yl}-2-(methanesulfonyloxy)benzoate (1.50 g), 3-hydroxy-1-phenyl-1H-pyrazole-4-carbaldehyde (0.56 g), potassium carbonate (0.41 g) and N,N-dimethylformamide (30 mL) was stirred at room temperature for 2 hrs. The reaction mixture was acidified by adding 1N hydrochloric acid, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated. The residue was subjected to silica gel column chromatography and eluted with ethyl acetate-hexane (1:3 to 1:1, v/v) 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-(methanesulfonyloxy)benzoate as pale-yellow crystals (0.80 g, yield 41%). Recrystallization from ethyl acetate-hexane gave pale-yellow prism crystals. melting point: 136-137° C.

Provenance & Evidence