Trifluoroacetic acid → {5-[3,5-bis(Trifluoromethyl)phenyl]-3-isoxazolyl}methanol

HRID 1188645Notes

Reaction equation

HRID 1188645 reaction equation
O1CCCCC1[O:7][CH2:8][C:9]1[CH:13]=[C:12]([C:14]2[CH:19]=[C:18]([C:20]([F:23])([F:22])[F:21])[CH:17]=[C:16]([C:24]([F:27])([F:26])[F:25])[CH:15]=2)[O:11][N:10]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[F:27][C:24]([F:25])([F:26])[C:16]1[CH:15]=[C:14]([C:12]2[O:11][N:10]=[C:9]([CH2:8][OH:7])[CH:13]=2)[CH:19]=[C:18]([C:20]([F:21])([F:22])[F:23])[CH:17]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 578004293-[(tetrahydro-2H-pyran-2-yloxy)methyl]-5-[3,5-bis(trifluoromethyl)phenyl]isoxazole

Product 1

HCID 57800356{5-[3,5-bis(Trifluoromethyl)phenyl]-3-isoxazolyl}methanolYield 69%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-[(tetrahydro-2H-pyran-2-yloxy)methyl]-5-[3,5-bis(trifluoromethyl)phenyl]isoxazole (Example 323A) (0.590 g, 1.49 mmol) in DCM (15 mL) was added TFA (1.5 mL). The reaction is stirred at rt overnight. Solvent and excess TFA were removed in vacuo. The residue was purified by radial chromatography (0-60% EtOAc-hexanes gradient) to afford the title compound (0.320 g, 69% yield): MS (ES) m/z 312 (M+1).

Workup

  1. customSolvent and excess TFA were removed in vacuo
  2. customThe residue was purified by radial chromatography (0-60% EtOAc-hexanes gradient)

Sources & evidence

ORD record
ord-dc55b679260243189746acac23be66cd
Source dataset
uspto-grants-2014_03
Patent number
US08673948B2

Reaction notes

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