Simple and Efficient Preparation of Reagents for Thiopyran Introduction: Methyl Tetrahydro-4-oxo-2H-thiopyran-3-carboxylate, Tetrahydro-4H-thiopyran-4-one, and 3, …

…, HM Gillis, GE Beye, V Jheengut, GT Achonduh

Index: Ward, Dale E.; Rasheed, M. Abdul; Gillis, H. Martin; Beye, Garrison E.; Jheengut, Vishal; Achonduh, George T. Synthesis, 2007 , # 10 p. 1584 - 1586

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Citation Number: 15

Abstract

Abstract Tetrahydro-4H-thiopyran-4-one was prepared in> 75% yield by treatment of dimethyl 3, 3′-thiobispropanoate with NaOMe (generated in situ) in THF solution and decarboxylation of the resulting methyl tetrahydro-4-oxo-2H-thiopyran-3-carboxylate in refluxing 10% aqueous H 2 SO 4. Reaction of tetrahydro-4H-thiopyran-4-one with Me 3 SiCl and Et 3 N in CHCl 3 gave the corresponding trimethylsilyl enol ether in near quantitative ...