[OH:1][C:2]1[C:3](=[O:10])[CH:4]=[C:5]([CH2:8][OH:9])[O:6][CH:7]=1.CC(C)([O-])C.[K+].[CH3:17][O:18][C:19]1[CH:26]=[CH:25][C:22]([CH2:23]Cl)=[CH:21][CH:20]=1>CN(C)C=O>[OH:9][CH2:8][C:5]1[O:6][CH:7]=[C:2]([O:1][CH2:23][C:22]2[CH:25]=[CH:26][C:19]([O:18][CH3:17])=[CH:20][CH:21]=2)[C:3](=[O:10])[CH:4]=1To a solution of 5-hydroxy-2-(hydroxymethyl)-4H-pyran-4-one (13.35 g, 94 mmol) in N,N-dimethylformamide (160 ml) stirred under nitrogen at 0° C. was added a solution of potassium tert-butoxide (12.65 g, 113 mmol) in N,N-dimethylformamide (40.0 ml) dropwise over 10 min. The mixture was then stirred at room temperature for 90 minute and 4-methoxybenzyl chloride (15.5 ml, 114 mmol) was added dropwise over 15 min and allowed to stir at 50° C. for 3 days. The reaction was cooled and concentrated under vacuum. Water (400 mL) was added, the resulting precipitate was filtered, washed with water, collected and dried to afford 2-(hydroxymethyl)-5-((4-methoxybenzyl)oxy)-4H-pyran-4-one (18.17 g, 69.3 mmol, 73.8% yield) as tan solid. LCMS: (M+H)+: 263.0
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