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

HRID 2102151Notes

Reaction equation

HRID 2102151 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-00ad8910b18c4257bfd5d157ee71b301
Source dataset
uspto-grants-2009_08
Patent number
US07572820B2

Reaction notes

Loading…