Tetrabutylammonium Fluoride → HCID 68591664, compound
Reaction equation
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.CC([Si](C1C=CC=CC=1)(C1C=CC=CC=1)[O:24][C:25]1[CH:26]=[C:27]2[C:32](=[CH:33][CH:34]=1)[C:31]([C:35]([NH:37][C:38]1[CH:43]=[C:42]([C:44]([F:47])([F:46])[F:45])[CH:41]=[C:40]([N:48]3[CH:52]=[C:51]([CH3:53])[N:50]=[CH:49]3)[CH:39]=1)=[O:36])=[CH:30][CH:29]=[CH:28]2)(C)C>O1CCCC1>[OH:24][C:25]1[CH:26]=[C:27]2[C:32](=[CH:33][CH:34]=1)[C:31]([C:35]([NH:37][C:38]1[CH:43]=[C:42]([C:44]([F:45])([F:46])[F:47])[CH:41]=[C:40]([N:48]3[CH:52]=[C:51]([CH3:53])[N:50]=[CH:49]3)[CH:39]=1)=[O:36])=[CH:30][CH:29]=[CH:28]2Participants
4
Procedure
A solution of tetrabutylammonium fluoride (3.5 mL of 1 M) in tetrahydrofuran is added to a stirred solution of 6[[(1,1-dimethylethyl)diphenylsilyl]oxy]-N-[3-(4-methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)phenyl]-1-naphthalenecarboxamide (1.91 g, 2.94 mmol) in tetrahydrofuran (50 mL) and the mixture is stirred at room temperature for 60 min. The solvent is evaporated off under reduced pressure and the residue is purified by column chromatography (SiO2; ethyl acetate) to afford the title compound as a cream solid m.p.: 169-172° C.