Hydrogen Peroxide → Indene oxide

HRID 2393879Notes

Reaction equation

HRID 2393879 reaction equation
[CH2:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.C1(N=C=NC2CCCCC2)CCCCC1.[OH:25]O>C(O)C>[CH2:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]2[O:25][CH:2]12

Participants

5

Reactant 3

HCID 784Hydrogen PeroxideHCID 7219IndeneHCID 10868Dicyclohexylcarbodiimide

Product 1

HCID 92838Indene oxideYield 98%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a mixture of indene (426 mg, 3.67 mmol), dicyclohexylcarbodiimide (150 mg, 0.73 mmol), hydrogen peroxide (1 mL of 30% aqueous, 9.8 mmol) and ethanol (5 mL) was added 10 mg of cation exchange resin (mild) beads. The reaction mixture was stirred at room temperature for twenty-four hours. Filtration removed the dicyclohexylurea and the resin beads. The filtrate was partitioned in a separatory funnel between ether (30 mL) and water (20 mL). Standard ethereal workup, followed by column chromatography on silica gel (elution with hexanes:ether, 10:1) afforded indene epoxide (94 mg, 98%).

Workup

  1. additionwas added 10 mg of cation exchange resin (mild) beads
  2. filtrationFiltration
  3. customremoved the dicyclohexylurea
  4. customThe filtrate was partitioned in a separatory funnel between ether (30 mL) and water (20 mL)

Sources & evidence

ORD record
ord-6119a9348dfe48329a5dd6e550949cd9
Source dataset
uspto-grants-1998_09
Patent number
US05808115

Reaction notes

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