1,4-Dioxane → HCID 59497139, compound

Participants

Reaction Steps

A solution of SeO2 (1.19 g, 10.8 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 4-(2-methoxy-ethoxy)-2-methyl-[1,10]phenanthroline (1.16 g, 4.3 mmol) in hot dioxane (30 mL) was added through an addition funnel over a period of 10 minutes and the reaction mixture was refluxed for 30 minutes. The solvent was evaporated in vacuo and the residue was treated with methylene chloride (200 mL) and saturated NaHCO3 (200 mL). The aqueous layer was extracted several times with methylene chloride (3×100 mL) and the combined organic layers were washed with brine, dried (Na2SO4), filtered and evaporated. The crude product was purified by flash chromatography (SiO2, MeOH/DCM, 1:40 to 1:20) to afford the pure product as a pale solid (0.65 g, 53%).

Provenance & Evidence