Selenium Dioxide → Ethyl 6-methoxy-1-oxo-3-phenyl-1H-indene-2-carboxylate

HRID 19522

Reaktionsgleichung

Reaktionsgleichung von HRID 19522
[CH2:1]([O:3][C:4]([C:6]1[CH2:7][C:8]2[C:13]([C:14]=1[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[CH:12][CH:11]=[C:10]([O:21][CH3:22])[CH:9]=2)=[O:5])[CH3:2].[Se](=O)=[O:24]>O1CCOCC1>[CH2:1]([O:3][C:4]([C:6]1[C:7](=[O:24])[C:8]2[C:13]([C:14]=1[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[CH:12][CH:11]=[C:10]([O:21][CH3:22])[CH:9]=2)=[O:5])[CH3:2]

Komponenten

4

Edukt 2

HCID 24007Selenium DioxideHCID 118451126-methoxy-3-phenyl-1H-indene-2-carboxylic acid ethyl ester

Produkt 1

HCID 23249734Ethyl 6-methoxy-1-oxo-3-phenyl-1H-indene-2-carboxylateAusbeute 72,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

6-Methoxy-3-phenyl-1H-indene-2-carboxylic acid ethyl ester (1 g, 3.39 mmol) prepared in Preparation Example 1 was dissolved in 1,4-dioxane and selenium dioxide (5.65 g, 50.96 mmol) was added thereto. The mixture was refluxed for 24 hrs, cooled, washed with 1M sodium bicarbonate, and 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 756 mg of the titled compound (yield: 72%) as a red solid.

Aufarbeitung

  1. temperatureThe mixture was refluxed for 24 hrs
  2. temperaturecooled
  3. washwashed with 1M sodium bicarbonate
  4. extractionextracted with diethyl ether
  5. customThe organic layer was separated
  6. dry with materialdried over anhydrous MgSO4
  7. concentrationconcentrated under a reduced pressure
  8. customThe resulting residue was purified by flash chromatography

Quellen und Nachweise

ORD-Eintrag
ord-99032a2ec70e43f3b3cc1844a780f592
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07745439B2

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