Tetrabutylammonium Fluoride → 6-Hydroxy-benzo[d]isoxazole-3-carboxylic acid (3-trifluoromethyl-phenyl)-amide
Reaction equation
[N+](CCCC)(CCCC)(CCCC)CCCC.[F-].[F:19][C:20]([F:51])([F:50])[C:21]1[CH:22]=[C:23]([NH:27][C:28]([C:30]2[C:34]3[CH:35]=[CH:36][C:37]([O:39][Si](C(C)C)(C(C)C)C(C)C)=[CH:38][C:33]=3[O:32][N:31]=2)=[O:29])[CH:24]=[CH:25][CH:26]=1>C1COCC1>[F:51][C:20]([F:19])([F:50])[C:21]1[CH:22]=[C:23]([NH:27][C:28]([C:30]2[C:34]3[CH:35]=[CH:36][C:37]([OH:39])=[CH:38][C:33]=3[O:32][N:31]=2)=[O:29])[CH:24]=[CH:25][CH:26]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
5.5 ml of a 1 M solution of Bu4NF in THF are added to a solution of 1.045 g (2.18 mMol) 6-triisopropylsilanyloxy-benzo[d]isoxazole-3-carboxylic acid (3-trifluoromethyl-phenyl)-amide dissolved in 25 ml THF. After 55 min, the solution is concentrated in vacuo, the residue redissolved in water and EtOAc, the aq. layer separated off and extracted twice with EtOAc. The organic layers are washed twice with water and brine, dried (Na2SO4) and concentrated. Trituration in hexane gives the title compound.