Acetonitrile → Ethyl 8-(2-ethoxycarbonyl-5,6-dimethoxy-4,7-dioxoindan-2-yl)octanoate

HRID 2268511Notes

Reaction equation

HRID 2268511 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]([O:62][CH2:63][CH3:64])=[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]([O:62][CH2:63][CH3:64])=[O:61])[CH2:37][C:38]2[C:39](=[O:51])[C:40]([O:49][CH3:50])=[C:41]([O:47][CH3:48])[C:42](=[O:45])[C:43]=2[CH2:44]1)=[O:35])[CH3:32]

Participants

5

Reactant 3

HCID 6342AcetonitrileHCID 180504Ceric ammonium nitrateHCID 18348627Ethyl 8-(2-ethoxycarbonyl-4,5,6,7-tetramethoxyindan-2-yl)octanoate

Product 1

HCID 18348669Ethyl 8-(2-ethoxycarbonyl-5,6-dimethoxy-4,7-dioxoindan-2-yl)octanoateYield 73.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A water (1 ml) solution of CAN (342 mg, 0.624 mmols) was dropwise added to an acetonitrile (2 ml) solution of ethyl 8-(2-ethoxycarbonyl-4,5,6,7-tetramethoxyindan-2-yl)octanoate (100 mg, 0.208 mmols), with cooling with ice. The reaction mixture was stirred for 15 minutes and water was added thereto, 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 only to hexane:ethyl acetate=4:1) to obtain the entitled compound (69 mg) as an oil.

Workup

  1. temperaturewith cooling with ice
  2. extractionwhich was 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 only to hexane

Sources & evidence

ORD record
ord-16cbbbfdff9a429d9d88a05952b00d0d
Source dataset
uspto-grants-2001_12
Patent number
US06326369B1

Reaction notes

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