L. Klemm, Jennifer J. Lu
Oct 1, 1991
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0
Influential Citations
2
Citations
Journal
Journal of Heterocyclic Chemistry
Abstract
The kinetics of hydrolysis of 7-acetyl-4-(1-carboethoxy-1-cyano)methylene-4,7-dihydrothieno[2,3-b]pyridine (1) in undried DMSO-d6 to give ethyl 2-(4-thieno[2,3-b]pyridyl)cyanoacetate and acetic acid at ambient temperature was investigated by 1H nmr spectrometry. The reaction is pseudo first order in the concentration of 1 with a rate constant of 9 × 10−4 per minute, not noticeably altered by the addition of deuteriotrifluoroacetic acid. The hydrolysis is, however, catalyzed by means of added pyridine-d5 (k = 37 × 10−4 per minute). The pyridine is presumed to serve as a transfer agent for the acetylium ion as in acetylations with acetyl chloride and acetic anhydride.