Sodium Carbonate → HCID 11212036, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 3-bromo-2-(4-methylsulfonylphenyl)-1-oxa-spiro[4,4]non-2-en-4-one (105 mg) in 5 ml of toluene and 15 ml ethanol, were added 20 mg of tetrakis(triphenylphosphine)palladium(0), 5 ml of 2 M aqueous sodium carbonate solution, and 50 mg of 4-isopropylbenzeneboronic acid. The reaction solution was stirred at 90° C. for 12 hours. The solvent was removed under reduced pressure and the resulting residue was extracted with 20 ml water and dichloromethane (30 ml×3). The organic layer was concentrated in vacuo and the resulting crude product was purified by column chromatography (hexane/ethylacetate) to obtain 87 mg of 3-(4-isopropyl-phenyl)-2-{4-(methylsulfonyl)phenyl}-1-oxa-spiro[4,4]non-2-en-4-one as a solid. mp: 139-140° C. NMR: δ1.25 (s, 3H), 1.27 (s, 3H), 2.04 (m, 6H), 2.15 (m, 2H), 2.92 (m, 1H), 3.06 (s, 3H), 7.21 (m, 4H), 7.83 (d, J=8.7 Hz, 2H), 7.93 (d, J=8.7 Hz, 2H). IR (cm−1): 2960, 1694, 1622, 1386, 1318, 1161, 768.

Provenance & Evidence