Selenium Dioxide → 5,6-methylenedioxy-1-oxo-3-phenyl-1H-indene-2-carboxylate ethyl ester

HRID 17881Notes

Reaction equation

HRID 17881 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][C:11]1[O:21][CH2:22][O:23][C:10]=1[CH:9]=2)=[O:5])[CH3:2].[Se](=O)=[O:25]>O1CCOCC1>[CH2:1]([O:3][C:4]([C:6]1[C:7](=[O:25])[C:8]2[C:13]([C:14]=1[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1)=[CH:12][C:11]1[O:21][CH2:22][O:23][C:10]=1[CH:9]=2)=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 24007Selenium DioxideHCID 68699725HCID 68699725, compound

Product 1

HCID 686989425,6-methylenedioxy-1-oxo-3-phenyl-1H-indene-2-carboxylate ethyl esterYield 70%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

5,6-Methylenedioxy-3-phenyl-1H-indene-2-carboxylate ethyl ester (3 g, 9.73 mmol) was dissolved in 1,4-dioxane. Selenium dioxide (10.8 g, 97.3 mmol) was added thereto and the reaction mixture was refluxed while stirring for 1 day, followed by cooling. The solution obtained after filtering residual solid selenium dioxide was combined with 1M sodium bicarbonate, and extracted with ether/water. The extract was dried over anhydrous magnesium sulfate, concentrated, and the resulting residue was purified by column chromatography to obtain 5,6-methylenedioxy-1-oxo-3-phenyl-1H-indene-2-carboxylate ethyl ester (2.18 g, yield 70%).

Workup

  1. temperaturethe reaction mixture was refluxed
  2. temperatureby cooling
  3. customThe solution obtained
  4. filtrationafter filtering residual solid selenium dioxide
  5. extractionextracted with ether/water
  6. dry with materialThe extract was dried over anhydrous magnesium sulfate
  7. concentrationconcentrated
  8. customthe resulting residue was purified by column chromatography

Sources & evidence

ORD record
ord-d6c34f8707e94405ab4916f21c8158a8
Source dataset
uspto-grants-2010_06
Patent number
US07741323B2

Reaction notes

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