Selenium Dioxide → 3-Chloro-5-vinyl-2,3'-bipyridine-6'-carbaldehyde

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Reaction Steps

4.0 g of 3-chloro-6′-methyl-5-vinyl-2,3′-bipyridine (14) (17.3 mmol) prepared in Example 10 was dissolved in 50 mL of 1,4-dioxane, and 5.8 g of selenium dioxide (52 mmol) was added thereto. The mixture was refluxed under heating and stirring for 18 hours, and cooled to room temperature. Then, the mixture was concentrated under reduced pressure, and dissolved in ethyl acetate to be washed with water. The organic layer was dried over magnesium sulfate, and concentrated under reduced pressure. The residue was separated by column chromatography (eluting solvent:ethyl acetate/hexane=1/4) to obtain 3.2 g of 3-chloro-5-vinyl-2,3′-bipyridine-6′-carbaldehyde (yield 75%).

Provenance & Evidence