Tetronic Acids and Derivatives Part VIII (1) o-Alkylation of 3-Unsubstituted Tetronic Acids |
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| Authors: | Suzanne Gelin Patrick Pollet |
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| Affiliation: | 1. Service de Chimie Organique, Institut National des Sciences Appliquees , Villeurbanne, 69621, France;2. Department of Chemistry , University of Petroleum and Minerals , P.O. Box 298, Dhahran, Saudi Arabia |
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| Abstract: | 4-methoxy-(5H)-furan-2-ones 1 are useful starting materials for the synthesis of naturally occuring lactones2. In a previous communication we have described an efficient entry to 4-alkoxy-(5H)-furan-2-ones 1–3 (alkyl tetronates) by lactonization of ethyl 4-acetoxy 3-ketoesters 4 using hydrochloric acid in several alcohols1. The detection of 4-hydroxy-(5H)-furan-2-ones 5 (tetronic acids) during the reaction course3 allowed us to postulate them as intermediates which were subsequently etherified to the products 1–3. In a very recent communication4, it was claimed that attempted alkylation of tetronic acids 5 using HC1 in an alcohol or alkyl halides on tetronic acids sodium salts are unsuccessful; moreover, the structure of our compounds 1–3 was questionned by arguing that isomeric 2-alkylated materials |
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