Hydrogen Peroxide → Octahydro-2H-pentaleno[1,6-bc]furan-2-one

HRID 50553Notes

Reaction equation

HRID 50553 reaction equation
[CH:1]12[CH:9]3[CH:3]([CH2:4][CH2:5][CH:6]3[CH2:7][CH2:8]1)[C:2]2=[O:10].C1C=CC(=O)/C(=C/NCCN/C=C2/C=CC=CC/2=[O:26])/C=1.OO>C(O)C>[CH:1]12[CH:9]3[CH:3]([CH2:4][CH2:5][CH:6]3[CH2:7][CH2:8]1)[C:2](=[O:10])[O:26]2

Participants

5

Reactant 3

HCID 784Hydrogen PeroxideHCID 12010634HCID 12010634, compoundHCID 178515945HCID 178515945, compound

Product 1

HCID 10307876Octahydro-2H-pentaleno[1,6-bc]furan-2-oneYield 617.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

Into 0.5 ml of ethanol was dissolved tricyclo[4,2,1,03,9]nonane-2-one (13.6 mg, 0.1 mmol). Into this ethanol solution was added the Co (III) (salen) complex (3.7 mg, 5 μmol) having the above formula (XI). Into this solution was added 30% hydrogen peroxide aqueous solution (15 μI, hydrogen peroxide content 0.13 mmol), which was stirred at room temperature for 24 hours. After the completion of the reaction, the mixed liquid was concentrated, and the residue was chromatographed in a silica gel column with hexane/ethyl acetate (=8/2) as a developing solvent, thereby obtaining 2-oxatricyclo[5.2.1.04,10]decane-3-one (4.7 mg, yield 31%) having the above formula (VIII). The enantiomer excess percentage of the product was determined as follows.

Workup

  1. customAfter the completion of the reaction
  2. concentrationthe mixed liquid was concentrated
  3. customthe residue was chromatographed in a silica gel column with hexane/ethyl acetate (=8/2) as a developing solvent

Sources & evidence

ORD record
ord-9f0654f057744021bbd1ae4e394cd7af
Source dataset
uspto-grants-2004_03
Patent number
US06713435B2

Reaction notes

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