Reaktion #47799

Reaktionsgleichung

compound

6-hydroxy-3-phenyl-1H-indene-2-carboxylic Acid Ethyl Ester

Selenium dioxide

→

titled compound

Ausbeute 61.0%

6-hydroxy-1-oxo-3-phenyl-1H-indene-2-carboxylic Acid Ethyl Ester

Ausbeute 61.0%

Lösungsmittel

1,4-dioxane

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturrefluxed for 10 hrs
2. 2
   Temperaturby cooling
3. 3
   WaschenThe resulting mixture washed with 1M sodium bicarbonate
4. 4
   Extraktionsuccessively extracted with diethyl ether
5. 5
   SonstigeThe organic layer was separated
6. 6
   Trocknendried over anhydrous MgSO4
7. 7
   Einengenconcentrated under a reduced pressure
8. 8
   SonstigeThe resulting residue was purified by flash chromatography

Vorschrift

The compound (16.00 g, 57.07 mmol) obtained in Step 2 was dissolved in 1,4-dioxane. Selenium dioxide (63.33 g, 570.07 mmol) was added thereto and refluxed for 10 hrs, followed by cooling. The resulting mixture washed with 1M sodium bicarbonate, and successively extracted with diethyl ether. The organic layer was separated, dried over anhydrous MgSO4, and concentrated under a reduced pressure. The resulting residue was purified by flash chromatography to obtain 10.198 g of the titled compound (yield: 61%) as a red solid.

Quelle