Acetone → Chromen-4-one, 3,5,7-trimethoxy-2-phenyl-

Participants

Reaction Steps

Galangin (27 mg, 0.1 mmol) was dissolved in dried acetone (20 mL), solid potassium carbonate (0.5 g) and dimethyl sulfate (1 mL) were added, and the mixture was refluxed for 4 hrs, then cooled to room temperature. The solution was filtered and evaporated, water (20 mL) and concentrated ammonium hydroxide (2 mL) were added and the solution was extracted with ethyl acetate (15 mL×2). The solvent was evaporated and the residue was recrystallized from methanol/water to give 21 mg product (67%). 1HNMR (DMSO-d6): d 3.73 (s, 3H, 3-OCH3), 3.86 (s, 3H, 7-OCH3), 3.86 (s, 3H, 5-OCH3), 6.48 (s, 1H, 8-H), 6.79 (s, 1H, 6-H), 7,99 (m, 3H), 8.02 (m, 2H). MS (CI/NH3): m/z 313 (MH+, base).

Provenance & Evidence