Acetonitrile → HCID 15552355, compound

HRID 2268522Notes

Reaction equation

HRID 2268522 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[O:32][C:33]1[C:41]([O:42][CH3:43])=[C:40]([O:44][CH3:45])[C:39]([O:46]C)=[C:38]2[C:34]=1[CH2:35][CH:36]([CH2:48][CH2:49][CH2:50][CH2:51][O:52][C:53]1[CH:63]=[CH:62][C:56]([C:57]([O:59][CH2:60][CH3:61])=[O:58])=[CH:55][CH:54]=1)[CH2:37]2>O>[CH3:43][O:42][C:41]1[C:33](=[O:32])[C:34]2[CH2:35][CH:36]([CH2:48][CH2:49][CH2:50][CH2:51][O:52][C:53]3[CH:63]=[CH:62][C:56]([C:57]([O:59][CH2:60][CH3:61])=[O:58])=[CH:55][CH:54]=3)[CH2:37][C:38]=2[C:39](=[O:46])[C:40]=1[O:44][CH3:45]

Participants

5

Reactant 3

HCID 6342AcetonitrileHCID 180504Ceric ammonium nitrateHCID 18348515HCID 18348515, compound

Product 1

HCID 15552355HCID 15552355, compoundYield 48.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A water (1.0 ml) solution of CAN (299 mg, 0.545 mmols) was dropwise added to an acetonitrile (2.0 ml) solution of ethyl 4-[4-(4,5,6,7-tetramethoxyindan-2-yl)butoxy]benzoate (100 mg, 0.218 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 out in vacuo, and the resulting crude product was purified by silica gel column chromatography (hexane:ethyl acetate=10:1 to 8:1) followed by recrystallization (from hexane-ethyl acetate) to obtain the entitled compound (45.0 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 out in vacuo
  6. customthe resulting crude product was purified by silica gel column chromatography (hexane:ethyl acetate=10:1 to 8:1)
  7. customfollowed by recrystallization (from hexane-ethyl acetate)

Sources & evidence

ORD record
ord-f598fa02b722412d87efce45c93e7de9
Source dataset
uspto-grants-2001_12
Patent number
US06326369B1

Reaction notes

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