Water → 5,7-Difluoro-1-(2-propen-1-yl)-2(1H)-quinolinone

Participants

Reaction Steps

A suspension of 5,7-difluoro-2(1H)-quinolinone (640 mg, 3.54 mmol) in DMF (15 ml) under argon at 0° C. was treated with sodium hydride (60% in mineral oil, 312 mg, 7.8 mmol) and then it was warmed up at rt. After 0.5 h at rt allyl iodide (0.72 mL, 7.8 mmol) was added. After 0.5 h sodium hydride (60% in mineral oil, 200 mg, 5 mmol) and allyl iodide (0.35 ml, 3.8 mmol) were added. Water (15 ml) was added and the aqueous was extracted using DCM (3×50 ml). The combined organic phases were dried, evaporated and the residue was chromatographed on silica gel, eluting with 0-4% MeOH-DCM to afford 350 mg of the desired compound (45%).

Provenance & Evidence