Triethylamine → 2-(5-Formyl-isoxazol-3-yl)-pyridine

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Reaction Steps

Sulfur trioxide pyridine (10.0 g, 62.8 mmol) was dissolved in dimethylsulfoxide (50 mL) and cooled to near 0° C. A solution of the compound prepared in Example 124 (5.05 g, 28.7 mmol) and triethylamine (16.0 mL, 115 mmol) in dichloromethane (40 mL) was added to the solution over 45 minutes. The reaction was warmed to room temperature and stirred overnight. The reaction was diluted with ethyl acetate and washed with sodium hydrogen carbonate aqueous solution. The organic phase was washed with water and dried over magnesium sulfate. The crude mixture was purified by column chromatography using an eluant of 1 to 3% ethyl acetate/dichloromethane to provide the title compound (0.90 g) with the following physical data.

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