Methyl 5-(chloromethyl)-2-furoate → Methyl 5-methyl-2-furancarboxylate

Participants

Reaction Steps

A solution of methyl 5-chloromethyl-2-furoate (5.0g, 28.7mmol) in ethyl acetate (40ml) was hydrogenated over 10% palladium on charcoal (50mg) for 3h. The catalyst was filtered off and washed with ethyl acetate. The combined filtrates were concentrated in vacuo and the residue purified by chromatography on silica gel eluting with 10% ethyl acetate in hexane to yield the title compound as a colourless oil (3.78g, 94%); vmax (CH2Cl2) 1725, 1534, 1522, 1437 and 1311cm-1 ; δH (CDCl3, 90MHz) 2.38 (3H, s), 3.86 (3H, s), 6.12 (1H, br d, J 4Hz) and 7.07 (1H, d, J 4Hz). [Mass spectrum: M+(140)].

Provenance & Evidence