Br[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:9][CH2:10][CH2:11][O:12][CH3:13])=[CH:4][CH:3]=1.[OH:14][C:15]1[CH:20]=[C:19]([CH3:21])[C:18]([C:22](=[O:24])[CH3:23])=[C:17]([CH3:25])[CH:16]=1.Cl.CN(C)CC(O)=O.C(=O)([O-])[O-].[Cs+].[Cs+]>O1CCOCC1.[Cu](I)I.O>[CH3:13][O:12][CH2:11][CH2:10][CH2:9][O:8][C:5]1[CH:6]=[CH:7][C:2]([O:14][C:15]2[CH:16]=[C:17]([CH3:25])[C:18]([C:22](=[O:24])[CH3:23])=[C:19]([CH3:21])[CH:20]=2)=[CH:3][CH:4]=1A mixture of 1-bromo-4-isopropoxybenzene (21-2, 0.85 g, 3.9 mmol), 1-(4-hydroxy-2,6-dimethylphenyl)ethanone (4-2, 1.10 g, 6.71 mmol), N,N-dimethylglycine HCl salt (0.21 g, 1.5 mmol), copper iodide (0.12 g, 0.60 mmol), and cesium carbonate (2.90 g, 8.91 mmol) in dioxane (15.0 mL) was stirred at 120° C. for 48 h. The reaction mixture was cooled to room temperature, added with water, and extracted with EtOAc. The organic layer was washed with brine, dried over anhydrous MgSO4, concentrated, and purified by flash column chromatography on silica gel (EtOAc:hexanes=1:5 as eluant) to give 1-{4-(4-(3-methoxypropoxy)phenoxy)-2,6-dimethylphenyl}ethanone (21-3, 0.27 g) as yellow oil in 21% yield: 1H NMR (CDCl3) δ 6.96 (dd, J=4.5, 2.2 Hz, 2 H), 6.89 (dd, J=4.3, 2.4 Hz, 2 H), 6.57 (s, 2 H), 4.05 (m, 2 H), 3.57 (t, J=6.2 Hz, 2H), 3.36 (s, 3 H), 2.66 (s, 3 H), 2.20 (s, 6 H), 2.05 (t, J=6.2 Hz, 2H).
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