p-Toluenesulfonic acid → 1-oxo-3-phenyl-6-(3-phenyl-propoxy)-1H-indene-2-carboxylic acid methyl ester

HRID 19539

Reaction equation

HRID 19539 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:7](=[O:31])[C:8]2[C:13]([C:14]=1[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[CH:12][CH:11]=[C:10]([O:21][CH2:22][CH2:23][CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[CH:9]=2)=[O:5])C.C1(C)C=CC(S(O)(=O)=O)=CC=1>CO>[CH3:1][O:3][C:4]([C:6]1[C:7](=[O:31])[C:8]2[C:13]([C:14]=1[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[CH:12][CH:11]=[C:10]([O:21][CH2:22][CH2:23][CH2:24][C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1)[CH:9]=2)=[O:5]

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 118452821-oxo-3-phenyl-6-(3-phenylpropoxy)-1H-indene-2-carboxylic acid ethyl ester

Product 1

HCID 687010351-oxo-3-phenyl-6-(3-phenyl-propoxy)-1H-indene-2-carboxylic acid methyl esterYield 62.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1-Oxo-3-phenyl-6-(3-phenylpropoxy)-1H-indene-2-carboxylic acid ethyl ester (2 g, 4.85 mmol) obtained in Example 7 was dissolved in methanol, p-toluenesulfonic acid (92 mg, 0.49 mmol) was added thereto, and refluxed for 24 hrs. The resulting mixture washed with sodium bicarbonate and extracted with ethyl acetate. The organic layer was separated, dried over anhydrous MgSO4 and concentrated under a reduced pressure. Then, the resulting residue was purified by flash chromatography to obtain 1.2 g of the titled compound (yield: 62%).

Workup

  1. temperaturerefluxed for 24 hrs
  2. washThe resulting mixture washed with sodium bicarbonate
  3. extractionextracted with ethyl acetate
  4. customThe organic layer was separated
  5. dry with materialdried over anhydrous MgSO4
  6. concentrationconcentrated under a reduced pressure
  7. customThen, the resulting residue was purified by flash chromatography

Sources & evidence

ORD record
ord-3c1bf3a9f67045bab896a8932ac5a56e
Source dataset
uspto-grants-2010_06
Patent number
US07745439B2

Linked notes

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