Reactions of Isopropenyl Stearate with Diethyl Malonate, Acetoacetic Ester, and Related Keto Esters. Enol Esters. XVII

Edward S. Rothman; Gordon G. Moore; Stephen S. Hecht

doi:10.1021/jo00954a025

Reactions of Isopropenyl Stearate with Diethyl Malonate, Acetoacetic Ester, and Related Keto Esters. Enol Esters. XVII

Edward S. Rothman, Gordon G. Moore, Stephen S. Hecht

Research output: Contribution to journal › Comment/debate › peer-review

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Abstract

The major product from the acid-catalyzed reaction of isopropenyl stearate with diethyl malonate is identified as the a-pyrone, 6-ethoxy-3-hexadecyI-4-stearoyloxy-2H-pyran-2-one. Alcoholysis of the 6-alkoxy a-pyrone proceeds unusually easily without requiring catalysis. Acetoacetic ester and 3-oxoglutarate esters react analogously with isopropenyl stearate to form a-pyrones.

Original language	English (US)
Pages (from-to)	2540-2543
Number of pages	4
Journal	Journal of Organic Chemistry
Volume	38
Issue number	14
DOIs	https://doi.org/10.1021/jo00954a025
State	Published - Jul 1 1973
Externally published	Yes

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abstract = "The major product from the acid-catalyzed reaction of isopropenyl stearate with diethyl malonate is identified as the a-pyrone, 6-ethoxy-3-hexadecyI-4-stearoyloxy-2H-pyran-2-one. Alcoholysis of the 6-alkoxy a-pyrone proceeds unusually easily without requiring catalysis. Acetoacetic ester and 3-oxoglutarate esters react analogously with isopropenyl stearate to form a-pyrones.",

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AU - Rothman, Edward S.

AU - Moore, Gordon G.

AU - Hecht, Stephen S.

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N2 - The major product from the acid-catalyzed reaction of isopropenyl stearate with diethyl malonate is identified as the a-pyrone, 6-ethoxy-3-hexadecyI-4-stearoyloxy-2H-pyran-2-one. Alcoholysis of the 6-alkoxy a-pyrone proceeds unusually easily without requiring catalysis. Acetoacetic ester and 3-oxoglutarate esters react analogously with isopropenyl stearate to form a-pyrones.

AB - The major product from the acid-catalyzed reaction of isopropenyl stearate with diethyl malonate is identified as the a-pyrone, 6-ethoxy-3-hexadecyI-4-stearoyloxy-2H-pyran-2-one. Alcoholysis of the 6-alkoxy a-pyrone proceeds unusually easily without requiring catalysis. Acetoacetic ester and 3-oxoglutarate esters react analogously with isopropenyl stearate to form a-pyrones.

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Reactions of Isopropenyl Stearate with Diethyl Malonate, Acetoacetic Ester, and Related Keto Esters. Enol Esters. XVII

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