反应详情

A mixture of 7-methoxy-2-naphthyl trifluoromethanesulfonate (3.15 g, 10.3 mmol), 4-methoxy-phenylboronic acid (2.2 g, 14 mmol) sodium carbonate (10 mL of 2N aqueous solution), tetrakis(triphenylphosphine)palladium (0.59 g, 0.05 mmol), and 100 mL ethylene glycol dimethyl ether were heated to reflux for 8 hr. The mixture was cooled to room temperature and poured into 100 mL of 1 N NaOH, The mixture was extracted with ethyl acetate (3×250 mL), washed with brine (2×100 mL), dried over magnesium sulfate, filtered, evaporation of the solvent and purification by silica chromatography (5%-10% ethyl acetate-hexanes) yielded 2.17 g (79%) of the title compound as a white solid: mp 154° C.; 1H NMR (CDCl3): δ 3.87 (3H, s), 3.94 (3H, s), 7.02 (2H, d, J=8.72 Hz), 7.13 (1H, dd, J=2.54 Hz, J=9.09 Hz), 7.18 (1H, d, J=2.55 Hz), 7.56 (1H, dd, J=1.82 Hz, J=8.36 Hz), 7.65 (2H, d, J=8.72 Hz), 7.74 (1H, d, J=9.09 Hz), 7.81 (1H, d, J=8.36 Hz), 7.89 (1H, d, J=1.09 Hz); MS (EI) m/z264 (M).

1. temperaturewere heated
2. temperatureto reflux for 8 hr
3. extractionThe mixture was extracted with ethyl acetate (3×250 mL)
4. washwashed with brine (2×100 mL)
5. dry with materialdried over magnesium sulfate
6. filtrationfiltered
7. customevaporation of the solvent and purification by silica chromatography (5%-10% ethyl acetate-hexanes)