(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

Participants

Reaction Steps

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.

Provenance & Evidence