Synthesis of functionalized hydroxyphthalides and their conversion to 3-cyano-1 (3H)-isobenzofuranones. The Diels-Alder reaction of methyl 4, 4-diethoxybutynoate …

…, GW Morrow, JS Swenton

Index: Freskos, John N.; Morrow, Gary W.; Swenton, John S. Journal of Organic Chemistry, 1985 , vol. 50, # 6 p. 805 - 810

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Citation Number: 87

Abstract

Several methods have been used in the preparation of functionalized hydroxyphthalides. Metalation of N, N-diethyl-3-methoxybenzamide, followed by reaction with dimethylformamide and hydrolysis, furnished 3-hydroxy-4-methoxy-l (3H)-isobenzofuranone in 52% yield. Reaction of the metalation product of m-fluorobenzaldehyde dimethyl acetal with carbon dioxide, followed by hydrolysis, gave 3-hydroxy-7-fluoro-l (3H)-iso- ...

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