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

Participants

Reaction Steps

A solution of methyl 5-chloromethyl-2-furoate (5.0 g, 28.7 mmol) in ethyl acetate (40 ml) was hydrogenated over 10% palladium on charcoal (50 mg) for 3 h. 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 (3.78 g, 94%); νmax (CH2Cl2) 1725, 1534, 1522, 1437 and 1311 cm-1 ; δHCDCl3, 90 MHz) 2.38 (3H, s), 3.86 (3H, s), 6.12 (1H, br d, J 4 Hz) and 7.07 (1H, d, J 4 Hz). [Mass spectrum: M+ (140)].

Provenance & Evidence