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 H2 SO4 . Reaction of tetrahydro-4H -thiopyran-4-one with Me3 SiCl and Et3 N in CHCl3 gave the corresponding trimethylsilyl enol ether in near quantitative yield. The prepared reagents are useful for the synthesis of thiopyran-containing compounds.
Key words
tetrahydro-4H -thiopyran-4-one - 4-thianone - heterocyclic ketone - Dieckmann cyclization - thiopyran synthesis
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