Potassium Carbonate → Isoflavone

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To a 100 mL round bottom flask was added genistein (500 mg, 1.85 mmol) and K2CO3 (1.02 g, 7.4 mmol). The flask was equipped with a reflux condenser and purged with N2. To the flask was added acetone (15 mL) and MeI (0.277 mL), and the reaction was heated to 59° C. Additional K2CO3 and MeI were added as needed to push the reaction. Upon completion, the reaction was allowed to cool to room temperature and was filtered to remove KI. Purified by flash column chromatography (SiO2, 2% MeOH/CH2Cl2) to afford 14 (260 mg, 45%) as an off-white solid. Analytical data for isoflavone 14: 1H NMR (500 MHz, CDCl3) δ 7.77 (s, 1H), 7.49 (d, J=9 Hz, 2H), 6.94 (d, J=9 Hz, 2H), 6.45 (s, 1H), 6.38 (s, 1H), 3.95 (s, 3H), 3.90 (s, 3H), 3.84 (s, 3H); 13C NMR (125 MHz, CDCl3) δ 175.7, 164.1, 161.7, 160.2, 159.6, 150.2, 130.6, 126.2, 124.6, 113.9, 110.2, 96.4, 92.7, 56.6, 56.0, 55.5; LCMS: Mass calculated for C18H16O5, [M+H]+, 313. Found 313.

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