p-Toluenesulfonic acid → HCID 10832317, compound

HRID 2399419Notes

Reaction equation

HRID 2399419 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:31][CH2:32]C)([O:28][CH2:29]C)OCC.C1(C)C=CC(S(O)(=O)=O)=CC=1>CO>[CH3:32][O:31][C:24]1([O:28][CH3:29])[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 31214Ethyl 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), triethyl orthoformate (0.21 mL, 1.9 mmol) and a catalytic amount of p-toluenesulfonic acid in methanol (20 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-52493326b6a34b8ab9b3b4a020268add
Source dataset
uspto-grants-1995_09
Patent number
US05449686

Reaction notes

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