Selenium Dioxide → (R)-8-(1-(tert-butyldimethylsilyloxy)propan-2-yloxy)quinoline-2-carbaldehyde

Participants

Reaction Steps

To a solution of (R)-8-(1-(tert-butyldimethylsilyloxy)propan-2-yloxy)-2-methylquinoline (0.33 g, 1.0 mmol) in dioxane (40 mL) and water (0.4 mL) was added selenium dioxide (0.13 g, 1.2 mmol) and the resultant mixture heated at reflux for 1 hour. The cooled reaction mixture was filtered through a plug of Celite® to remove solids, rinsing with dichloromethane and the filtrate was concentrated under reduced pressure. The residue was purified by normal phase chromatography on silica gel (10% ethyl acetate/hexanes) providing the title compound (0.29 g, 84%).

Provenance & Evidence