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

HRID 341658Notes

Reaction equation

HRID 341658 reaction equation
[CH2:1]([O:3][CH2:4][C@@:5]12[O:12][C@@H:9]([CH:10]=[CH:11]1)[C:8](=[O:13])[CH2:7][C:6]2=[O:14])[CH3:2].[H][H]>C(OCC)(=O)C.[Pd]>[CH2:1]([O:3][CH2:4][C@@:5]12[O:12][C@@H:9]([CH2:10][CH2:11]1)[C:8](=[O:13])[CH2:7][C:6]2=[O:14])[CH3:2]

Participants

5

Reactant 2

HCID 68732506(1S*,5S*)-1-ethoxymethyl-8-oxabicyclo[3.2.1]oct-6-ene-2,4-dioneHCID 178418361HCID 178418361, compound

Product 1

HCID 68730659(1S*,5S*)-1-ethoxymethyl-8-oxabicyclo[3.2.1]octane-2,4-dioneYield 82.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (1S*,5S*)-1-ethoxymethyl-8-oxabicyclo[3.2.1]oct-6-ene-2,4-dione (2.8 g, 0.014 mol) in ethyl acetate (10 ml) is added 10% palladium on carbon (0.056 g), followed by stirring under a 1 bar hydrogen atmosphere for 24 hours. The reaction mixture is then filtered through diatomaceous earth and the filtrate is concentrated under reduced pressure. The residue is purified by column chromatography on silical gel to afford (1S*,5S*)-1-ethoxymethyl-8-oxabicyclo[3.2.1]octane-2,4-dione (2.3 g) as a pale yellow solid.

Workup

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

Sources & evidence

ORD record
ord-2610440ae36a4f3f95929f6bb75b3a0b
Source dataset
uspto-grants-2014_11
Patent number
US08895761B2

Reaction notes

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