Hydrochloric Acid → Methyl 1-[4-(5-methyl-2-phenyl-4-oxazolylmethoxy)benzyl]-4-phenylpyrrole-3-carboxylate

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Reaction Steps

Sodium hydride (60%, oily, 298 mg) was added to a mixture of methyl 4-phenylpyrrole-3-carboxylate (1.50 g), 4-(4-chloromethylphenoxymethyl)-5-methyl-2-phenyloxazole (2.34 g) and N,N-dimethylformamide (15 ml) at 0° C., and the mixture was stirred for one hour. The reaction mixture was poured into dilute hydrochloric acid, which was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated aqueous sodium chloride solution, dried (MgSO4), and then concentrated. The residue was subjected to silica gel column chromatography, and methyl 1-[4-(5-methyl-2-phenyl-4-oxazolylmethoxy)benzyl]-4-phenylpyrrole-3-carboxylate (3.12 g, yield: 88%) was obtained as colorless crystals from the fraction eluted with ethyl acetate-hexane (1:3, volume ratio). This was recrystallized from ethyl acetate-hexane. Melting point: 115–116° C.

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