Sodium Carbonate → 2,2-dimethyl-4-(4-methoxyphenyl)-5-{4-(methylsulfonyl)phenyl}-3(2H)-furanone

Participants

Reaction Steps

To a stirred solution of 4-bromo-2,2-dimethyl-5-{4-(methylsulfonyl)phenyl}-3(2H)-furanone (220 mg), 1,3-bis(diphenylphosphino)propane (24 mg) and palladium(II) acetate (6.1 mg) in 30 ml benzene, were added 2 M aqueous sodium carbonate (0.22 ml) and 4-methoxybenzeneboronic acid (90 mg). The reaction solution was kept at reflux for 24 hours. Then the solvent was removed under reduced pressure. The resulting residue was purified by a procedure similar to the purification method in Example 2 to yield 55 mg of 2,2-dimethyl-4-(4-methoxyphenyl)-5-{4-(methylsulfonyl)phenyl}-3(2H)-furanone as a solid. NMR: δ1.56 (s, 6H), 3.07 (s, 3H), 3.83 (s, 3H), 6.92 (d, J=8.7 Hz, 2H), 7.23 (d, J=9.0 Hz, 2H), 7.89(dd, J=8.7, 8.7 Hz, 4H). IR (cm−1): 2925, 1697, 1592, 1149, 1031, 912, 745.

Provenance & Evidence