Tetrabutylammonium Fluoride → 6-Hydroxy-benzo[d]isoxazole-3-carboxylic acid (3-trifluoromethyl-phenyl)-amide

HRID 556347Notes

Reaction equation

HRID 556347 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]=1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 669929826-Triisopropylsilanyloxy-benzo[d]isoxazole-3-carboxylic acid (3-trifluoromethyl-phenyl)-amide

Product 1

HCID 1363466276-Hydroxy-benzo[d]isoxazole-3-carboxylic acid (3-trifluoromethyl-phenyl)-amide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

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.

Workup

  1. concentrationthe solution is concentrated in vacuo
  2. dissolutionthe residue redissolved in water
  3. customEtOAc, the aq. layer separated off
  4. extractionextracted twice with EtOAc
  5. washThe organic layers are washed twice with water and brine
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-e735cfcfc0bd428fbb95b48558b79d4e
Source dataset
uspto-grants-2011_11
Patent number
US08058276B2

Reaction notes

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