Water → HCID 57570907, compound

Participants

Reaction Steps

To a cooled (0° C.) solution of chelidamic acid diethyl ester (Chaubet, F.; Nguyen van duong, M.; Gref, A.; Courtieu, J.; Crumbliss, A. L.; Gaudemer, A. Tetrahedron Lett. 1990, 31(40), 5729-5732) (3.5 g) in pyridine (35 mL), was added dropwise trifluoromethanesulfonyl chloride (2.6 mL). The reaction was then stirred at room temperature for 3 hours. Water and ethyl acetate were added. The layers were separated, and the aqueous layer was extracted twice ethyl acetate. The combined organic solutions were dried over magnesium sulfate, and concentrated in vacuo to a residue. The residue was purified by silica gel chromatography (Merck SuperVarioPrep 90g column, Si60 15-40μm), eluted with dichloromethane to give 4-trifluoromethanesulfonyloxy-pyridine-2,6-dicarboxylic acid diethyl ester (4.2g).

Provenance & Evidence