Br[C:2]1[C:3](=[O:9])[CH2:4][CH2:5][C:6]=1[O:7][CH3:8].[CH2:10]([O:17][C:18]1[CH:23]=[C:22]([CH3:24])[C:21](B(O)O)=[C:20]([CH3:28])[CH:19]=1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].C1(P(C2CCCCC2)C2C=CC=CC=2C2C(OC)=CC=CC=2OC)CCCCC1>C1(C)C=CC=CC=1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH2:10]([O:17][C:18]1[CH:23]=[C:22]([CH3:24])[C:21]([C:2]2[C:3](=[O:9])[CH2:4][CH2:5][C:6]=2[O:7][CH3:8])=[C:20]([CH3:28])[CH:19]=1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1To a suspension of 2-bromo-3-methoxycyclopent-2-enone (5.00 g, 26.0 mmol), 4-benzyloxy-2,6-dimethylphenyl boronic acid (7.20 g, 28 mmol) (described in EP1726580) and potassium phosphate (9.55 g, 45 mmol) in degassed toluene (125 ml) is added palladium (II) acetate (0.135 g, 0.6 mmol) and 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (0.492 g, 1.2 mmol). The reaction mixture is then heated at 90° C. under a nitrogen atmosphere for 4 hours, then allowed to cool to room temperature. After partitioning between ethyl acetate (500 ml) and distilled water (500 ml), the organic phase is separated and concentrated in vacuo. The crude product is purified by flash column chromatography (ethyl acetate/hexane eluant) to afford 2-(4-benzyloxy-2,6-dimethylphenyl)-3-methoxycyclopent-2-enone as a white solid.
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