Ethyl (E)-3-(5,6-Dihydro-2H-pyran-3-yl)acrylate → Ethyl 3-(tetrahydro-2H-pyran-3-yl)propanoate

Participants

Reaction Steps

The above was repeated in the exact same fashion with a second batch. Hence a solution of ethyl (2E)-3-(5,6-dihydro-2H-pyran-3-yl)-2-propenoate (2.59 g) and palladium on carbon (147 mg, 10% wet) in ethyl acetate (65 ml) was hydrogenated at atmospheric pressure and room temperature. The hydrogen uptake (˜715 ml) was complete after 15 minutes. The catalyst was filtered through celite and the filtrate concentrated in vacuo. to afford a pale yellow oil which was combined with that of the first batch (5.34 g). This was purified by silica chromatography (120 g) (ISCO) using a gradient elution of 0-10% cyclohexane:ethyl acetate to afford the title compound as a clear oil (4.61 g).

Provenance & Evidence