Pyridine → acetyl Sumiki's acid

Participants

Reaction Steps

A mixture of 5-hydroxymethylfuran-2-carboxylic acid (5.90 g), dry dichloromethane (100 ml), pyridine (6.71 ml), 4-dimethylaminopyridine (507 mg), and acetic anhydride (4.21 ml) was stirred for 2 hours at room temperature. The mixture was diluted with ethyl acetate and washed with 5M hydrochloric acid and brine (3 times), dried (MgSO4), and evaporated. The residue was re-evaporated twice from dry toluene to give the title acid as a solid (5.00 g); δH [(CD3)2CO] 2.05 (3H, s), 5.11 (2H, s), 6.62 (1H, d, J 4 Hz), 7.17 (1H, d, J 4 Hz) and 8.31 (1H, br S).

Provenance & Evidence