Selenium Dioxide → 6-hydroxy-1-oxo-3-phenyl-1H-indene-2-carboxylic acid ethyl ester

HRID 17874

Reaction equation

HRID 17874 reaction equation
[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]([OH:21])[CH:9]=2)=[O:5])[CH3:2].[Se](=O)=[O:23]>O1CCOCC1>[CH2:1]([O:3][C:4]([C:6]1[C:7](=[O:23])[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]([OH:21])[CH:9]=2)=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 24007Selenium DioxideHCID 118452786-hydroxy-3-phenyl-1H-indene-2-carboxylic acid ethyl ester

Product 1

HCID 118452796-hydroxy-1-oxo-3-phenyl-1H-indene-2-carboxylic acid ethyl esterYield 58%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

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.

Workup

  1. temperatureThe mixture was refluxed for 12 hour with vigorous stirring
  2. filtrationThe resulting mixture was filtered
  3. concentrationconcentrated
  4. extractionthe concentrate was extracted with ethyl acetate
  5. washThe extract was washed with brine
  6. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  7. concentrationconcentrated under a reduced pressure

Sources & evidence

ORD record
ord-9317969a1a364c05ade6516d6d0ab071
Source dataset
uspto-grants-2010_06
Patent number
US07741323B2

Linked notes

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