Tetrabutylammonium Fluoride → HCID 68528437, compound
Reaction equation
[Si]([O:8][CH2:9][CH2:10][CH:11]([N:19]1[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][C:26]=2[F:28])[C:21]([CH3:30])([CH3:29])[C:20]1=[O:31])[C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([F:18])[CH:13]=1)(C(C)(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[F:28][C:26]1[CH:25]=[CH:24][CH:23]=[C:22]2[C:27]=1[N:19]([CH:11]([C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([F:18])[CH:13]=1)[CH2:10][CH2:9][OH:8])[C:20](=[O:31])[C:21]2([CH3:30])[CH3:29]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
1-[3-{[tert-butyl(dimethyl)silyl]oxy}-1-(3-fluorophenyl)propyl]-7-fluoro-3,3-dimethyl-1,3-dihydro-2H-indol-2-one (0.80 g, 1.8 mmol) was dissolved in tetrahydrofuran and tetrabutyl ammonium fluoride (1.0 M in THF, 5.3 mL, 5.3 mmol) was added and the mixture was stirred for 1 hour. Reaction was quenched with saturated aqueous ammonium chloride then saturated sodium bicarbonate was added, diluted with ether, washed with water, and saturated brine. The organic layer was separated, dried over anhydrous magnesium sulfate, filtered, and concentrated in vacuo. The crude product was purified via Isco chromatography (Redisep, silica, gradient 5-50% ethyl acetate in hexane) to afford 0.58 g (97%) racemic 7-fluoro-1-[1-(3-fluorophenyl)-3-hydroxypropyl]-3,3-dimethyl-1,3-dihydro-2H-indol-2-one that was resolved by chiral HPLC.