Continuous Processing to Control a Potentially Hazardous Process: Conversion of Aryl 1, 1-Dimethylpropargyl Ethers to 2, 2-Dimethylchromenes (2, 2-Dimethyl-2 H-1- …

RJ Bogaert-Alvarez, P Demena…

Index: Bogaert-Alvarez, Ricardo J.; Demena, Paul; Kodersha, Gus; Polomski, Robert E.; Soundararajan; Wang, Steve S. Y. Organic Process Research and Development, 2001 , vol. 5, # 6 p. 636 - 645

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Citation Number: 27

Abstract

The thermal Claisen rearrangement of 4-cyanophenyl 1, 1-dimethylpropargyl ether (4) to 6- cyano-2, 2-dimethylchromene (5),(6-cyano-2, 2-dimethyl-2 H-1-benzopyran), which is used in the synthesis of a potassium channel activator drug candidate, BMS-180448, created a significant process development issue. The resulting large heat release in this conversion posed not only a safety risk but could also cause product degradation if done in a batch- ...

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