p-Toluenesulfonic acid → HCID 71138308, compound

HRID 587293Notes

Reaction equation

HRID 587293 reaction equation
[N:1]1([C:6]2[CH:11]=[CH:10][C:9]([C:12](O)([CH2:14][CH:15]([C:20]3[CH:25]=[C:24]([Cl:26])[CH:23]=[C:22]([Cl:27])[CH:21]=3)[C:16]([F:19])([F:18])[F:17])[CH3:13])=[CH:8][CH:7]=2)[CH:5]=[N:4][CH:3]=[N:2]1.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[Cl:26][C:24]1[CH:25]=[C:20]([CH:15]([C:16]([F:17])([F:19])[F:18])/[CH:14]=[C:12](/[C:9]2[CH:10]=[CH:11][C:6]([N:1]3[CH:5]=[N:4][CH:3]=[N:2]3)=[CH:7][CH:8]=2)\[CH3:13])[CH:21]=[C:22]([Cl:27])[CH:23]=1

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 71138338HCID 71138338, compound

Product 1

HCID 71138308HCID 71138308, compoundYield 31.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 2-(4-(1H-1,2,4-triazol-1-yl)phenyl)-4-(3,5-dichlorophenyl)-5,5,5-trifluoropentan-2-ol (100 mg, 0.233 mmol) in toluene was added a catalytic amount of p-toluenesulfonic acid and the water was removed by azeotropic distillation over the course of 12 h. The reaction mixture was cooled to room temperature and dissolved in EtOAc. The solution was washed with sat aqueous NaHCO3 solution and brine, dried over Na2SO4 and concentrated under reduced pressure. Purification by column chromatography (SiO2, 100-200 mesh; 20%-25% EtOAc in petroleum ether) afforded the title compound as a solid (30 mg, 31%).

Workup

  1. customthe water was removed by azeotropic distillation over the course of 12 h
  2. dissolutiondissolved in EtOAc
  3. washThe solution was washed with sat aqueous NaHCO3 solution and brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated under reduced pressure
  6. customPurification by column chromatography (SiO2, 100-200 mesh; 20%-25% EtOAc in petroleum ether)

Sources & evidence

ORD record
ord-a6e535cc580447a0930d72db6b5de3ac
Source dataset
uspto-grants-2016_01
Patent number
US09226500B2

Reaction notes

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