O.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.C([Si](C)(C)[N:25]1[C:33]2[C:28](=[CH:29][C:30]([O:34][Si](C(C)(C)C)(C)C)=[CH:31][CH:32]=2)[C:27]([CH2:42][CH3:43])=[CH:26]1)(C)(C)C>C1COCC1.C(OCC)(=O)C>[CH2:42]([C:27]1[C:28]2[C:33](=[CH:32][CH:31]=[C:30]([OH:34])[CH:29]=2)[NH:25][CH:26]=1)[CH3:43]Tetrabutylammonium fluoride hydrate (1.4 g, 4.3 mmol) was added to an ice-cooled solution of 1-(tert-butyl-dimethyl-silanyl)-5-(tert-butyl-dimethyl-silanyloxy)-3-ethyl-1H-indole (840 mg, 2.2 mmol) in THF (8 ml). The reaction mixture was stirred for 45 min at ambient temperature, diluted with ethyl acetate and washed with 1 N HCl and water. The organic phase was concentrated under reduced pressure and the crude product purified by column chromatography (silica gel, ethyl acetate/heptane 1:2) to give 258 mg (1.6 mmol, 74%) 3-ethyl-1H-indol-5-ol.
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