Pyridine → 7-Propyl-3-(trifluoromethyl)-1,2-benzisoxazol-6-yl trifluoromethanesulfonate

HRID 1245336Notes

Reaction equation

HRID 1245336 reaction equation
[OH:1][C:2]1[CH:14]=[CH:13][C:5]2[C:6]([C:9]([F:12])([F:11])[F:10])=[N:7][O:8][C:4]=2[C:3]=1[CH2:15][CH2:16][CH3:17].N1C=CC=CC=1.[O:24](S(C(F)(F)F)(=O)=O)[S:25]([C:28]([F:31])([F:30])[F:29])(=O)=[O:26].[OH-].[Na+]>C(Cl)Cl>[F:29][C:28]([F:31])([F:30])[S:25]([O:1][C:2]1[CH:14]=[CH:13][C:5]2[C:6]([C:9]([F:12])([F:11])[F:10])=[N:7][O:8][C:4]=2[C:3]=1[CH2:15][CH2:16][CH3:17])(=[O:26])=[O:24]

Participants

6

Reactant 4

HCID 1049PyridineHCID 14798Sodium HydroxideHCID 67749Trifluoromethanesulfonic anhydrideHCID 1358008127-Propyl-3-(trifluoromethyl)benzo[d]isoxazol-6-ol

Product 1

HCID 219109917-Propyl-3-(trifluoromethyl)-1,2-benzisoxazol-6-yl trifluoromethanesulfonate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 6-hydroxy-7-propyl-3-(trifluoromethyl)-1,2-benzisoxazole (500 mg, 2.04 mmol) in dry CH2Cl2 was added pyridine (0.82 mL, 10.2 mmol) at 0° C. under N2. Tf2O was then added dropwise to the reaction mixture and the resulting mixture stirred for 30 min. 1N NaOH was added and the mixture extracted with CH2Cl2. Combined organic extracts were washed with brine, dried over Na2SO4 and the solvent evaporated in vacuo. The residue was purified by chromatography on silica gel using ethyl acetate and hexane (10:90) to give the title compound.

Workup

  1. extractionthe mixture extracted with CH2Cl2
  2. washCombined organic extracts were washed with brine
  3. dry with materialdried over Na2SO4
  4. customthe solvent evaporated in vacuo
  5. customThe residue was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-cf6d99fd02ae4b25bd9646c52642beb4
Source dataset
uspto-grants-2006_10
Patent number
US07125865B2

Reaction notes

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