Reaktion #46152

Reaktionsgleichung

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

selenium dioxide

→

title compound

Ausbeute 58.0%

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

Ausbeute 58.0%

Lösungsmittel

1,4-dioxane

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe mixture was refluxed for 12 hour with vigorous stirring
2. 2
   FiltrationThe resulting mixture was filtered
3. 3
   Einengenconcentrated
4. 4
   Extraktionthe concentrate was extracted with ethyl acetate
5. 5
   WaschenThe extract was washed with brine
6. 6
   Trocknenthe organic layer was dried over anhydrous magnesium sulfate
7. 7
   Einengenconcentrated under a reduced pressure

Vorschrift

6-Hydroxy-3-phenyl-1H-indene-2-carboxylate ethyl ester (1 g, 3.57 mmol) was dissolved in 1,4-dioxane (50 ml), and then selenium dioxide (5.49 g, 53.55 mmol) was added thereto. The mixture was refluxed for 12 hour with vigorous stirring. The resulting mixture was filtered and concentrated, and the concentrate was extracted with ethyl acetate. The extract was washed with brine, and the organic layer was dried over anhydrous magnesium sulfate, concentrated under a reduced pressure, and the residue was subjected to silica gel column chromatography (ethyl acetate:hexane=1:4) to obtain the title compound (58%) as a rich red solid.

Quelle