Imidazole → 3-((Tert-butyldimethylsilyl)oxy)-6-fluoro-1-indanone

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[OH:1][CH:2]1[C:10]2[C:5](=[CH:6][C:7]([F:11])=[CH:8][CH:9]=2)[C:4](=[O:12])[CH2:3]1.[Si:13](Cl)([C:16]([CH3:19])([CH3:18])[CH3:17])([CH3:15])[CH3:14].N1C=CN=C1>CN(C)C=O>[Si:13]([O:1][CH:2]1[C:10]2[C:5](=[CH:6][C:7]([F:11])=[CH:8][CH:9]=2)[C:4](=[O:12])[CH2:3]1)([C:16]([CH3:19])([CH3:18])[CH3:17])([CH3:15])[CH3:14]

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실험 절차

A solution of 3-hydroxy-6-fluoro-1-indanone (4.09 g, 24.6 mmoles) in dimethylformamide (10 mL) was added to a solution of tert-butyldimethylsilyl chloride (4.60 g, 30.5 mmoles, Aldrich) and imidazole (4.22 g, 62.0 mmoles, Aldrich) in dimethylformamide (20 mL). The solution was stirred at ambient temperature for 18 hours and evaporated in vacuo. The residue was dissolved in dichloromethane (200 mL) and washed with water (6×75 mL) and brine (100 mL), dried over magnesium sulfate, filtered and evaporated in vacuo. The residue was chromatographed on silica gel eluting with hexane: ethyl acetate (95:5). The fractions containing the major spot were combined and evaporated in vacuo, and the residue was dried in a vacuum at ambient temperature for 18 hours to give 4.14 g (60%) of 3-((tert-butyldimethylsilyl)oxy)-6-fluoro-1-indanone as a white solid, mp 56°-58° C.;