[OH:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[CH:5][NH:6]2.N1C=CN=C1.[Si:16](Cl)([C:19]([CH3:22])([CH3:21])[CH3:20])([CH3:18])[CH3:17].O>CN(C=O)C>[Si:16]([O:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[CH:5][NH:6]2)([C:19]([CH3:22])([CH3:21])[CH3:20])([CH3:18])[CH3:17]4-Hydroxyindole (831 mg, 6.24 mmol) was dissolved in DMF (8.0 mL), and the solution was added with imidazole (510 mg, 7.49 mmol) and tert-butyldimethylsilyl chloride (1.03 g, 6.86 mmol), followed by stirring at room temperature for 5 hours. The reaction mixture was added with water and extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by flash column chromatography (hexane/ethyl acetate=85/15) to obtain 4-(tert-butyldimethylsilyloxy)indole (1.53 g, 99%).
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