Methanol → (7-Fluoro-2-oxo-1(2H)-quinolinyl)acetaldehyde

Participants

Reaction Conditions

Reaction Steps

A solution of 7-fluoro-1-(2-propen-1-yl)-2(1H)-quinolinone (5.0 g, 0.025 mmol) in 3:1 CH2Cl2:MeOH (500 mL) was cooled to −70° and 03 was bubbled through the solution for 20 min. Dimethyl sulfide (19 mL, 0.25 mol) were added and the reaction was stirred for 90 min at −70° C., then allowed to warm to room temperature overnight. The solvents were removed under reduced pressure yielding a thick orange oil. Purification by column chromatography on silica gel (1% to 100% hexane:ethyl acetate gradient) yielded a dark yellow solid (4.2 g, 82%).

Provenance & Evidence