1,4-Dioxane → 7-(2-(Tert-butyldimethylsilyloxy)ethoxy)-6-fluoroquinoline-2-carbaldehyde

Participants

Reaction Steps

To a solution of 7-(2-(tert-butyldimethylsilyloxy)ethoxy)-6-fluoro-2-methylquinoline (2.74 g, 8.17 mmol) in dioxane (24 mL) and water (0.24 mL) was added SeO2 (0.997 g, 8.98 mmol). The reaction mixture was heated at reflux for 4 hours. After cooling to ambient temperature, the solid was removed by filtration and washed with DCM. The filtrate was concentrated under reduced pressure and The residue was purified by flash chromatography on silica gel (4:1 hexanes/EtOAc) to give 7-(2-(tert-butyldimethylsilyloxy)ethoxy)-6-fluoroquinoline-2-carbaldehyde (2.69 g, 94%).

Provenance & Evidence