Acetonitrile → 8-(2-Hydroxymethyl-5,6-dimethoxy-4,7-dioxoindan-2-yl)octanol

HRID 2268516Notes

Reaction equation

HRID 2268516 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.[OH:31][CH2:32][C:33]1([CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH2:56][CH2:57][OH:58])[CH2:41][C:40]2[C:35](=[C:36]([O:48]C)[C:37]([O:46][CH3:47])=[C:38]([O:44][CH3:45])[C:39]=2[O:42]C)[CH2:34]1>O>[OH:31][CH2:32][C:33]1([CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH2:56][CH2:57][OH:58])[CH2:41][C:40]2[C:39](=[O:42])[C:38]([O:44][CH3:45])=[C:37]([O:46][CH3:47])[C:36](=[O:48])[C:35]=2[CH2:34]1

Participants

5

Reactant 3

HCID 6342AcetonitrileHCID 180504Ceric ammonium nitrateHCID 183485878-(2-Hydroxymethyl-4,5,6,7-tetramethoxyindan-2-yl)octanol

Product 1

HCID 183486558-(2-Hydroxymethyl-5,6-dimethoxy-4,7-dioxoindan-2-yl)octanolYield 25.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A water (1.0 ml) solution of CAN (509 mg, 0.928 mmols) was dropwise added to an acetonitrile (4.0 ml) solution of 8-(2-hydroxymethyl-4,5,6,7-tetramethoxyindan-2-yl)octanol (147 mg, 0.371 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=2:1 to 1:2) followed by recrystallization from hexane-ethyl acetate to obtain the entitled compound (35 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=2:1 to 1:2)
  7. customfollowed by recrystallization from hexane-ethyl acetate

Sources & evidence

ORD record
ord-5eeda64b353543cda701ac42bd17eaeb
Source dataset
uspto-grants-2001_12
Patent number
US06326369B1

Reaction notes

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