5-{4-[(Phenylmethyl)oxy]-1-buten-1-yl]-3,6-dihydro-2H-pyran → 4-(Tetrahydro-2H-pyran-3-yl)-1-butanol

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Reaction Steps

A solution of 5-{4-[(phenylmethyl)oxy]-1-buten-1-yl}-3,6-dihydro-2H-pyran (2.03 g) and 10% palladium on carbon (88 mg) in ethyl acetate (83 ml) was hydrogenated at atmospheric pressure and room temperature. Hydrogen uptake (˜500 ml) was complete after 15 hours. The catalyst was filtered through celite and the filtrate concentrated in vacuo to afford a colourless oil. Analysis by 1H-NMR showed that the benzyl group was present in the majority of the compound. Hydrogenation was continued under the same conditions for a further 24 hours with additional hydrogen uptake of ˜300 ml. The catalyst was filtered through celite and the filtrate concentrated in vacuo to afford the title compound as a colourless oil (1.21 g).

Provenance & Evidence