Reaction #46153

Reaction equation

6-Hydroxy-1-oxo-3-phenyl-1H-indene-2-carboxylate ethyl ester

3-phenylpropanol

triphenylphosphine

Diethyl azodicarboxylate

→

title compound

Yield 85.0%

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

Yield 85.0%

Solvents

tetrahydrofuran

tetrahydrofuran

Conditions

Workup

1. 1
   workup.ADDITIONwas added dropwise
2. 2
   Otherat 0° C
3. 3
   Washthe mixture was washed with brine
4. 4
   Extractionextracted with ethyl acetate
5. 5
   Dryingthe extract was dried over anhydrous magnesium sulfate
6. 6
   Concentrationthe concentrated under a reduced pressure
7. 7
   Otherthe residue was purified by silica gel column chromatography (diethyl ether:hexane=1:10)

Procedure

6-Hydroxy-1-oxo-3-phenyl-1H-indene-2-carboxylate ethyl ester (1.7 g, 6.07 mmol), 3-phenylpropanol (1.65 g, 12.14 mmol) and triphenylphosphine (3.18 g, 12.14 mmol) were dissolved in tetrahydrofuran (100 ml). Diethyl azodicarboxylate (2 ml, 12.14 mmol) dissolved in tetrahydrofuran (20 ml) was added dropwise thereto at 0° C. After stirring for 6 hours at room temperature, the mixture was washed with brine, extracted with ethyl acetate, the extract was dried over anhydrous magnesium sulfate, the concentrated under a reduced pressure, and the residue was purified by silica gel column chromatography (diethyl ether:hexane=1:10) to obtain the title compound (yield 85%) as a dark red solid.

Source