Reaction #47817

Reaction equation

1-Oxo-3-phenyl-6-(3-phenylpropoxy)-1H-indene-2-carboxylic acid ethyl ester

p-toluenesulfonic acid

→

titled compound

Yield 62.1%

1-oxo-3-phenyl-6-(3-phenyl-propoxy)-1H-indene-2-carboxylic Acid Methyl Ester

Yield 62.1%

Solvents

methanol

Conditions

Workup

1. 1
   Temperaturerefluxed for 24 hrs
2. 2
   WashThe resulting mixture washed with sodium bicarbonate
3. 3
   Extractionextracted with ethyl acetate
4. 4
   OtherThe organic layer was separated
5. 5
   Dryingdried over anhydrous MgSO4
6. 6
   Concentrationconcentrated under a reduced pressure
7. 7
   OtherThen, the resulting residue was purified by flash chromatography

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%).

Source