1,4-Dioxane → 2-Oxo-2H-pyrano[2,3-b]pyridine-7-carbaldehyde

Participants

Reaction Conditions

Reaction Steps

To a solution of 7-methyl-2H-pyrano[2,3-b]pyridin-2-one (160 mg, 0.98 mmol) in 1,4-dioxane (12 mL) in a microwave reaction vial was added SeO2 (328 mg, 3.0 mmol). The reaction vial was capped and the mixture was heated in a microwave at 160° C. for 90 minutes. The reaction was diluted with DCM, filtered through a pad of Celite® and concentrated. The resulting material was dissolved in DCM and loaded onto a plug of silica gel and evaporated. Purification by column chromatography (silica gel) using a DCM/MeOH gradient (0-10% MeOH) provided the desired product as a pale yellow solid (120 mg, 40%). LCMS (ES+) m/z 176 (MH+).

Provenance & Evidence