1,4-Dioxane → HCID 59497123, compound

Participants

Reaction Steps

A solution of SeO2 (1.01 g, 9.1 mmol) in a mixture of dioxane (50 mL) and water (2 mL) was heated to reflux in a two-neck 250 mL round-bottomed flask. A solution of 2-methyl-4-ethoxy-[1,10]phenanthroline (0.87 g, 3.6 mmol) in hot dioxane (50 mL) was added through an addition funnel over a period of 30 minutes and the reaction mixture was refluxed for 1 hour. The reaction mixture was filtered while hot and the residue rinsed with more hot dioxane (20 mL) and filtered. The filtrates were combined and concentrated in vacuo and the residue was treated with methylene chloride (100 mL) and a 10% K2CO3 aqueous solution (100 mL). The aqueous layer was extracted with methylene chloride (3×100 mL) and the combined organic layers were washed with brine, dried (Na2SO4), filtered and concentrated. The crude product was purified by flash chromatography (SiO2, MeOH/DCM, 1:30 to 1:15) to afford the pure product as a light brown solid (0.15 g, 16%).

Provenance & Evidence