p-Toluenesulfonic acid → HCID 23222722, compound

HRID 1780853Notes

Reaction equation

HRID 1780853 reaction equation
[C:1]([C:3]1([C:10]2[CH:15]=[CH:14][C:13]([O:16][CH:17]([F:19])[F:18])=[C:12]([O:20][CH:21]([F:23])[F:22])[CH:11]=2)[CH2:8][CH2:7]C(=O)[CH2:5][CH2:4]1)#[N:2].[CH:24]([O:29][CH3:30])([O:27][CH3:28])OC.C1(C)C=CC(S(O)(=O)=O)=CC=1>CO>[CH3:30][O:29][C:24]1([O:27][CH3:28])[CH2:5][CH2:4][C:3]([C:10]2[CH:15]=[CH:14][C:13]([O:16][CH:17]([F:18])[F:19])=[C:12]([O:20][CH:21]([F:22])[F:23])[CH:11]=2)([C:1]#[N:2])[CH2:8][CH2:7]1

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 9005Trimethyl orthoformateHCID 15295198HCID 15295198, compound

Product 1

HCID 23222722HCID 23222722, compoundYield 98.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 4-cyano-4-(3,4-bisdifluoromethoxyphenyl)cyclohexan-1-one (1.34 g, 4.05 mmol), trimethyl orthoformate (0.53 mL, 4.85 mmol) and a catalytic amount of p-toluenesulfonic acid in methanol (40 mL) was heated gently under an argon atmosphere for 2 h. The mixture was cooled and then concentrated. The residue was partitioned between 5% aqueous sodium carbonate and ethyl acetate, was extracted twice with ethyl acetate, the organic extract was dried (potassium carbonate) and the solvent was removed in vacuo to provide an oil (1.5 g, 98%).

Workup

  1. temperatureThe mixture was cooled
  2. concentrationconcentrated
  3. customThe residue was partitioned between 5% aqueous sodium carbonate and ethyl acetate
  4. extractionwas extracted twice with ethyl acetate
  5. extractionthe organic extract
  6. dry with materialwas dried (potassium carbonate)
  7. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-85aca9eecad0414385a4059a9159f302
Source dataset
uspto-grants-1997_05
Patent number
US05631286

Reaction notes

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