Reaction #46174

Reaction equation

3-Phenyl-6-(3-phenylpropyloxy)-1-oxo-1H-indene-2-carboxylate ethyl ester

p-toluene sulfonic acid

→

title compound

Yield 75.3%

3-phenyl-6-(3-phenylpropyloxy)-1-oxo-1H-indene-2-carboxylate methyl ester

Yield 75.3%

Solvents

methanol

Conditions

Workup

1. 1
   OtherThe mixture was reacted for 1 hour at 70° C.
2. 2
   Washwashed with brine
3. 3
   ExtractionThe organic layer was extracted with ethyl acetate
4. 4
   Dryingdried over anhydrous sulfonate sulfate
5. 5
   Concentrationconcentrated
6. 6
   Otherthe resulting residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:9)

Procedure

3-Phenyl-6-(3-phenylpropyloxy)-1-oxo-1H-indene-2-carboxylate ethyl ester (1.65 g, 4.0 mmol) prepared in (Step 5) of Example 1 was dissolved in methanol (160 ml) and p-toluene sulfonic acid (228 mg, 1.2 mmol) was added thereto. The mixture was reacted for 1 hour at 70° C., and then washed with brine. The organic layer was extracted with ethyl acetate, dried over anhydrous sulfonate sulfate, concentrated, and the resulting residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:9) to obtain the title compound (yield 75.3%) as a red solid.

Source