D. E. Ward, M. Rasheed, H. M. Gillis
Feb 28, 2007
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Synthesis
Abstract
Tetrahydro-4 H-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-2 H-thiopyran-3-carboxylate in refluxing 10% aqueous H 2 SO 4 . Reaction of tetrahydro-4 H-thiopyran-4-one with Me 3 SiCl and Et 3 N in CHCl 3 gave the corresponding trimethylsilyl enol ether in near quantitative yield. The prepared reagents are useful for the synthesis of thiopyran-containing compounds.