A Convenient Method for Preparation of 2-(Methylthio)alkanoic Acids and Their Related Compounds Using the Carbanions of Substituted Malonic Esters
Starting from alkyl- or aryl-substituted malonic esters prepared by various methods, 2-(methylthio)alkanoic acids are synthesized by successive treatment with sodium ethoxide and with S-methyl methanethiosulfonate, followed by alkaline hydrolysis which causes concurrent decarboxylation.Production of 2-(phenylthio)alkanoic acids is also achieved in a similar manner.
A NOVEL METHOD FOR PREPARATION OF 2-(METHYL- OR PHENYLTHIO)ALKANOIC ESTERS
Ethyl 2-acetylalkanoate gave ethyl 2-(methyl- or phenylthio)alkanoate in high yield on treatment with CH3SSO2CH3, PhSSO2Ph, or PhSSPh in the presence of small excess of EtONa in EtOH.Application of the present method to synthesis of pellitorine and thr queen substance is also described.