[OH:1][C:2]1[C:3](=[O:10])[CH:4]=[C:5]([CH2:8][OH:9])[O:6][CH:7]=1.C(=O)([O-])[O-].[K+].[K+].Cl[CH2:18][C:19]1[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=1>CN(C=O)C>[OH:9][CH2:8][C:5]1[O:6][CH:7]=[C:2]([O:1][CH2:18][C:19]2[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=2)[C:3](=[O:10])[CH:4]=1To a solution of 5-hydroxy-2-(hydroxymethyl)-4H-pyran-4-one (Alfa Aesar, 5.11 g, 35.96 mmol) in DMF (70 mL) at room temperature was added potassium carbonate (9.94 g, 71.92 mmol) and 1-(chloromethyl)-4-methoxybenzene (5.86 mL, 43.15 mmol) dropwise. The reaction mixture was heated at 80° C. for 1 hour then concentrated. To the resulting slurry was added ice water. The precipitate was collected by filtration then triturated with ethyl acetate and filtered again. The title compound was obtained as a tan solid (6.44 g, 68%).
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