Acetonitrile → 8-(2-Ethoxycarbonyl-5,6-dimethoxy-4,7-dioxoindan-2-yl)octanoic acid

HRID 2268513Notes

Reaction equation

HRID 2268513 reaction equation
O=[N+]([O-])[O-].[O-][N+](=O)[O-].[O-][N+](=O)[O-].[O-][N+](=O)[O-].[O-][N+](=O)[O-].[O-][N+](=O)[O-].[Ce+4].[NH4+].[NH4+].C(#N)C.[CH2:31]([O:33][C:34]([C:36]1([CH2:53][CH2:54][CH2:55][CH2:56][CH2:57][CH2:58][CH2:59][C:60]([OH:62])=[O:61])[CH2:44][C:43]2[C:38](=[C:39]([O:51]C)[C:40]([O:49][CH3:50])=[C:41]([O:47][CH3:48])[C:42]=2[O:45]C)[CH2:37]1)=[O:35])[CH3:32]>O>[CH2:31]([O:33][C:34]([C:36]1([CH2:53][CH2:54][CH2:55][CH2:56][CH2:57][CH2:58][CH2:59][C:60]([OH:62])=[O:61])[CH2:44][C:43]2[C:42](=[O:45])[C:41]([O:47][CH3:48])=[C:40]([O:49][CH3:50])[C:39](=[O:51])[C:38]=2[CH2:37]1)=[O:35])[CH3:32]

Participants

5

Reactant 3

HCID 6342AcetonitrileHCID 180504Ceric ammonium nitrateHCID 183486378-(2-Ethoxycarbonyl-4,5,6,7-tetramethoxyindan-2-yl)octanoic acid

Product 1

HCID 155523508-(2-Ethoxycarbonyl-5,6-dimethoxy-4,7-dioxoindan-2-yl)octanoic acidYield 68%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A water (1 ml) solution of CAN (238 mg, 0.435 mmols) was dropwise added to an acetonitrile (2 ml) solution of 8-(2-ethoxycarbonyl-4,5,6,7-tetramethoxyindan-2-yl)octanoic acid (78.6 mg, 0.174 mmols) with cooling with ice and then stirring was continued for 15 minutes. Water was added to the reaction mixture, which was then extracted with ethyl acetate. The organic layer was washed with a saturated aqueous sodium chloride solution and then dried. The solvent was evaporated in vacuo and the resulting crude product was purified by silica gel column chromatography (hexane:ethyl acetate=4:1 to ethyl acetate only) to obtain the entitled compound (50 mg) as an oil.

Workup

  1. temperaturewith cooling with ice
  2. extractionwas then extracted with ethyl acetate
  3. washThe organic layer was washed with a saturated aqueous sodium chloride solution
  4. customdried
  5. customThe solvent was evaporated in vacuo
  6. customthe resulting crude product was purified by silica gel column chromatography (hexane

Sources & evidence

ORD record
ord-f3335647d96e453a83c0ed9c7a7eee4e
Source dataset
uspto-grants-2001_12
Patent number
US06326369B1

Reaction notes

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