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

HRID 2268512Notes

Reaction equation

HRID 2268512 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.[C:31]([C:34]1([CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH2:56][CH2:57][C:58]([OH:60])=[O:59])[CH2:42][C:41]2[C:36](=[C:37]([O:49]C)[C:38]([O:47][CH3:48])=[C:39]([O:45][CH3:46])[C:40]=2[O:43]C)[CH2:35]1)([OH:33])=[O:32]>O>[C:31]([C:34]1([CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH2:56][CH2:57][C:58]([OH:60])=[O:59])[CH2:42][C:41]2[C:40](=[O:43])[C:39]([O:45][CH3:46])=[C:38]([O:47][CH3:48])[C:37](=[O:49])[C:36]=2[CH2:35]1)([OH:33])=[O:32]

Participants

5

Reactant 3

HCID 6342AcetonitrileHCID 180504Ceric ammonium nitrateHCID 183486098-(2-Carboxy-4,5,6,7-tetramethoxyindan-2-yl)octanoic acid

Product 1

HCID 155523518-(2-Carboxy-5,6-dimethoxy-4,7-dioxoindan-2-yl)octanoic acidYield 38.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A water (1 ml) solution of CAN (287 mg, 0.523 mmols) was dropwise added to an acetonitrile (2 ml) solution of 8-(2-carboxy-4,5,6,7-tetramethoxyindan-2-yl)octanoic acid (88.6 mg, 0.209 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=1:1 to ethyl acetate only) followed by recrystallization from hexane-ethyl acetate to obtain the entitled compound (32 mg) as crystals.

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
  7. customethyl acetate=1:1 to ethyl acetate only) followed by recrystallization from hexane-ethyl acetate

Sources & evidence

ORD record
ord-bae2158437e44a5dbc84eff2d7e2157e
Source dataset
uspto-grants-2001_12
Patent number
US06326369B1

Reaction notes

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