Réaction #46153

Équation de réaction

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

3-phenylpropanol

triphenylphosphine

Diethyl azodicarboxylate

→

title compound

Rendement 85.0%

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

Rendement 85.0%

Solvants

tetrahydrofuran

tetrahydrofuran

Conditions de réaction

Traitement

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

Mode opératoire

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