(1R*,5S*)-1-methyl-8-oxabicyclo[3.2.1]oct-6-ene-2,4-dione → (1R*,5S*)-1-methyl-8-oxabicyclo[3.2.1]octane-2,4-dione

HRID 341643Notes

Reaction equation

HRID 341643 reaction equation
[CH3:1][C@@:2]12[O:9][C@@H:6]([CH:7]=[CH:8]1)[C:5](=[O:10])[CH2:4][C:3]2=[O:11].[H][H]>C(OCC)(=O)C.[Pd]>[CH3:1][C@@:2]12[O:9][C@@H:6]([CH2:7][CH2:8]1)[C:5](=[O:10])[CH2:4][C:3]2=[O:11]

Participants

5

Reactant 2

HCID 67523953(1R*,5S*)-1-methyl-8-oxabicyclo[3.2.1]oct-6-ene-2,4-dioneHCID 178418361HCID 178418361, compound

Product 1

HCID 67533518(1R*,5S*)-1-methyl-8-oxabicyclo[3.2.1]octane-2,4-dioneYield 56.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (1R*,5S*)-1-methyl-8-oxabicyclo[3.2.1]oct-6-ene-2,4-dione (12.0 g, 0.079 mol) in ethyl acetate (100 ml) is added 10% palladium on carbon (2.4 g), followed by stirring under a 1 bar hydrogen atmosphere for 24 hours. The reaction mixture is then filtered through diatomaceous earth and concentrated under reduced pressure. The residue is purified by column chromatography on silica gel to afford (1R*,5S*)-1-methyl-8-oxabicyclo[3.2.1]octane-2,4-dione (6.90 g) as pale yellow solid.

Workup

  1. filtrationThe reaction mixture is then filtered through diatomaceous earth
  2. concentrationconcentrated under reduced pressure
  3. customThe residue is purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-8d236863ebd943cf965d0e45ed13f96d
Source dataset
uspto-grants-2014_11
Patent number
US08895761B2

Reaction notes

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