Water → Methyl 2-(5-methyl-2-phenyl-4-oxazolyl)methoxy-4-pyridinecarboxylate

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Reaction Steps

To a solution of 5-methyl-2-phenyl-4-oxazolylmethanol (9.46 g) in N,N-dimethylformamide (50 ml) was added, sodium hydride (60% in oil, 2.40 g) at 0° C. and the mixture was stirred for 15 min. Then a solution (50 ml) of methyl 2-chloro-4-pyridinecarboxylate (8.58 g) in tetrahydrofuran was added. After stirring at room temperature for 1 hr., the reaction mixture was poured into water and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine, dried (MgSO4) and concentrated. The residue was subjected to silica gel column chromatography, and methyl 2-(5-methyl-2-phenyl-4-oxazolylmethoxy)-4-pyridinecarboxylate (2190 mg, yield 14%) was obtained as colorless crystals from a fraction eluted with ethyl acetate-hexane (1:3, volume ratio). The crystals were recrystallized from ethyl acetate-hexane. melting point: 106–107° C.

Provenance & Evidence