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

HRID 19521Notes

Reaction equation

HRID 19521 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 61%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

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.

Workup

  1. temperaturerefluxed for 10 hrs
  2. temperatureby cooling
  3. washThe resulting mixture washed with 1M sodium bicarbonate
  4. extractionsuccessively extracted 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

Sources & evidence

ORD record
ord-4c12d6e0994842cbb40a85decb3a3cbd
Source dataset
uspto-grants-2010_06
Patent number
US07745439B2

Reaction notes

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