Acetonitrile → HCID 18348566, compound

HRID 2268518Notes

Reaction equation

HRID 2268518 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][CH2:52][CH2:53][CH2:54][C:55]([O:57][CH2:58][CH3:59])=[O:56])[CH2:37]2>O>[CH3:45][O:44][C:40]1[C:39](=[O:46])[C:38]2[CH2:37][CH:36]([CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][C:55]([O:57][CH2:58][CH3:59])=[O:56])[CH2:35][C:34]=2[C:33](=[O:32])[C:41]=1[O:42][CH3:43]

Participants

5

Reactant 3

HCID 6342AcetonitrileHCID 180504Ceric ammonium nitrateHCID 18348610HCID 18348610, compound

Product 1

HCID 18348566HCID 18348566, compoundYield 16.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A water (1.0 ml) solution of CAN (336 mg, 0.613 mmols) was dropwise added to an acetonitrile (2.0 ml) solution of ethyl 8-(4,5,6,7-tetramethoxyindan-2-yl)octanoate (100 mg, 0.245 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 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=8:1) followed by recrystallization from hexane to obtain the entitled compound (15 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:ethyl acetate=8:1)
  7. customfollowed by recrystallization from hexane

Sources & evidence

ORD record
ord-479d8ea81007427b9ec399e9749ac1f5
Source dataset
uspto-grants-2001_12
Patent number
US06326369B1

Reaction notes

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