Acetonitrile → HCID 18348629, compound

HRID 2268524Notes

Reaction equation

HRID 2268524 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:61]=[CH:60][C:56]([C:57]([OH:59])=[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:54]=[CH:55][C:56]([C:57]([OH:59])=[O:58])=[CH:60][CH:61]=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 18348557HCID 18348557, compound

Product 1

HCID 18348629HCID 18348629, compoundYield 53.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A water (2.0 ml) solution of CAN (1.27 g, 2.32 mmols) was dropwise added to an acetonitrile (8.0 ml) solution of 4-[4-(4,5,6,7-tetramethoxyindan-2-yl)butoxy]benzoic acid (400 mg, 0.929 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 (ethyl acetate) followed by recrystallization (from hexane-ethyl acetate) to obtain the entitled compound (200 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 (ethyl acetate)
  7. customfollowed by recrystallization (from hexane-ethyl acetate)

Sources & evidence

ORD record
ord-b9eeae1372704ba4a2920c93a3e9676c
Source dataset
uspto-grants-2001_12
Patent number
US06326369B1

Reaction notes

Loading…