We plan to synthesize Pyrdinium-CH2C(O)CO2X (where X could be a proton or a pyridinium ion) by the method of Arthur Green and Raymond Delaby ("Pyridinium and thiazolium salts with multifunctional propyl side chain" Bull Soc Chim France 1955, pp. 697-699). My student translated this article. It seems straightforward (solvent is diethyl ether), except for one problem. The mass of bromopyruvic acid (MW 166.96) is 16.7 g, and the mass of pyridine (MW 79.1) is 1.7 g). This works out to 100 mmols of bromopyruvic cid, and 21.5 mols of pyridine. In other words, the bromopyruvic acid is almost 5-fold in excess, which strikes me as odd.
One possibility is that the mass of pyridine is a typo, and there should be 17 grams of pyridine, which would provide just over a twofold excess of pyridine. A second equivalent of pyridine might be expected to deprotonate the carboxylic acid, which might facilitate the reaction. Any suggestions on the best way to proceed?