(2E)-3-(furan-3-yl)prop-2-enoic acid → 3-(Oxolan-3-yl)propanoic acid

A solution of (2E)-3-(3-furanyl)-2-propenoic acid (4.75 g, 34.4 mmol) and 10% palladium on carbon (0.366 g, 3.44 mmol) in ethyl acetate (100 ml) was hydrogentated at atmospheric pressure and room temperature for 72 hours. Hydrogen uptake ˜1.4 L (expected 2.4 L). The catalyst was filtered through Celite and concentrated in vacuo to give a brown oil. Analysis by 1H-NMR showed that the some material still contained the furan ring. Hydrogenation was continued under the same conditions with fresh catalyst for a further 24 hours with additional hydrogen uptake of 400 ml. The catalyst was filtered through Celite and the filtrate concentrated in vacuo to afford the title compound as a colourless oil (4.73 g).

1. filtrationThe catalyst was filtered through Celite
2. concentrationconcentrated in vacuo
3. customto give a brown oil
4. filtrationThe catalyst was filtered through Celite
5. concentrationthe filtrate concentrated in vacuo

ORD record

ord-a066e5dd958d4381b557ab085958f4c3

Source dataset

uspto-grants-2011_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07977344B2