Methanol → HCID 59321526, compound

Participants

Reaction Steps

A 0.5 N solution of sodium methoxide in methanol (2.8 mL, 1.4 mmol) was added to a solution of methyl isobutyrylacetate (0.19 mL, 1.34 mmol) in THF (0.24 mL) at 0° C. A solution of the crude N-hydroxy-2,4-dimethyl-3-pyridinecarboximidoyl chloride (0.22 g, 1.2 mmol) in THF (2.2 mL) was added and the resulting mixture was allowed to warm to room temperature and stir overnight. The solution was concentrated and the residue was partitioned between ethyl acetate and brine. The organic layer was dried with MgSO4, filtered and concentrated. The residue was chromatographed (silica gel, hexane to 3:2 ethyl acetate:hexane) to provide methyl 3-(2,4-dimethyl-3-pyridinyl)-5-(1-methylethyl)-4-isoxazolecarboxylate (0.17 g, 52%). ESI-LCMS m/z 275 (M+H)+.

Provenance & Evidence