Acetonitrile → HCID 18348608, compound

HRID 2268519Notes

Reaction equation

HRID 2268519 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][CH2:55][OH:56])[CH2:37]2>O>[OH:56][CH2:55][CH2:54][CH2:53][CH2:52][CH2:51][CH2:50][CH2:49][CH2:48][CH:36]1[CH2:35][C:34]2[C:33](=[O:32])[C:41]([O:42][CH3:43])=[C:40]([O:44][CH3:45])[C:39](=[O:46])[C:38]=2[CH2:37]1

Participants

5

Reactant 3

HCID 6342AcetonitrileHCID 180504Ceric ammonium nitrateHCID 18348590HCID 18348590, compound

Product 1

HCID 18348608HCID 18348608, compoundYield 26.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A water (1.0 ml) solution of CAN (463 mg, 0.845 mmols) was dropwise added to an acetonitrile (3.0 ml) solution of 8-(4,5,6,7-tetramethoxyindan-2-yl)octanol (138 mg, 0.338 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 out in vacuo, and the resulting crude product was purified by silica gel column chromatography (hexane:ethyl acetate=4:1 to 2:1) followed by recrystallization from hexane-diethyl ether to obtain the entitled compound (29.8 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 out in vacuo
  6. customthe resulting crude product was purified by silica gel column chromatography (hexane:ethyl acetate=4:1 to 2:1)
  7. customfollowed by recrystallization from hexane-diethyl ether

Sources & evidence

ORD record
ord-5c1f954a268b42d5bec4a68c732b9ced
Source dataset
uspto-grants-2001_12
Patent number
US06326369B1

Reaction notes

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