Acetonitrile → Ethyl 2-(4-benzyloxyphenyl)-5,6-dimethoxy-4,7-dioxo-2-indancarboxylate

HRID 2268520Notes

Reaction equation

HRID 2268520 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:38][C:39]1[CH:44]=[CH:43][C:42]([C:45]2([C:62]([O:64][CH2:65][CH3:66])=[O:63])[CH2:53][C:52]3[C:47](=[C:48]([O:60]C)[C:49]([O:58][CH3:59])=[C:50]([O:56][CH3:57])[C:51]=3[O:54]C)[CH2:46]2)=[CH:41][CH:40]=1)[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1>O>[CH2:31]([O:38][C:39]1[CH:40]=[CH:41][C:42]([C:45]2([C:62]([O:64][CH2:65][CH3:66])=[O:63])[CH2:46][C:47]3[C:48](=[O:60])[C:49]([O:58][CH3:59])=[C:50]([O:56][CH3:57])[C:51](=[O:54])[C:52]=3[CH2:53]2)=[CH:43][CH:44]=1)[C:32]1[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=1

Participants

5

Reactant 3

HCID 6342AcetonitrileHCID 180504Ceric ammonium nitrateHCID 18348586Ethyl 2-(4-benzyloxyphenyl)-4,5,6,7-tetramethoxy-2-indancarboxylate

Product 1

HCID 15552353Ethyl 2-(4-benzyloxyphenyl)-5,6-dimethoxy-4,7-dioxo-2-indancarboxylateYield 54.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A water (1.0 ml) solution of CAN (976 mg, 1.78 mmols) was dropwise added to an acetonitrile (7.0 ml) solution of ethyl 2-(4-benzyloxyphenyl)-4,5,6,7-tetramethoxy-2-indancarboxylate (350 mg, 0.711 mmols) with cooling with ice and 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 water and 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=5:1) followed by recrystallization from hexane-ethyl acetate to obtain the entitled compound (178 mg) as crystals.

Workup

  1. temperaturewith cooling with ice
  2. extractionwas then extracted with ethyl acetate
  3. washThe organic layer was washed with water
  4. dry with materiala saturated aqueous sodium chloride solution, and then dried
  5. customThe solvent was evaporated in vacuo
  6. customthe resulting crude product was purified by silica gel column chromatography (hexane:ethyl acetate=5:1)
  7. customfollowed by recrystallization from hexane-ethyl acetate

Sources & evidence

ORD record
ord-3af06506c80f456ba4a389ae5b5055a9
Source dataset
uspto-grants-2001_12
Patent number
US06326369B1

Reaction notes

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