p-Toluenesulfonic acid → HCID 10832317, compound

HRID 1780845Notes

Reaction equation

HRID 1780845 reaction equation
[C:1]([C:3]1([C:10]2[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[C:12]([O:18][CH:19]3[CH2:23][CH2:22][CH2:21][CH2:20]3)[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:1]#[N:2])([C:10]2[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[C:12]([O:18][CH:19]3[CH2:23][CH2:22][CH2:21][CH2:20]3)[CH:11]=2)[CH2:8][CH2:7]1

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 9005Trimethyl orthoformateHCID 9861604SB-200473

Product 1

HCID 10832317HCID 10832317, compoundYield 99.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 4-cyano-4-(3-cyclopentyloxy-4-methoxyphenyl)cyclohexan-1-one (0.5 g, 1.6 mmol), trimethyl orthoformate (0.21 mL, 1.9 mmol) and a catalytic amount of p-toluenesulfonic acid in methanol (2.0 mL) was heated gently under an argon atmosphere for 2 h. The mixture was cooled, was partitioned between 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 (0.57 g, 99%).

Workup

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

Sources & evidence

ORD record
ord-34ab3b9e253f4ebca113aa310c751823
Source dataset
uspto-grants-1997_05
Patent number
US05631286

Reaction notes

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