Synthesis of S-methyl 2-hydroxyalkanethioates, 2-hydroxyalkanoic acids and related compounds via the addition reaction of tris(methylthio)methanide ion to alkanals.

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概要

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• In connection with the studies on biological activities on myrmicacin and related compounds, the synthetic method for 2-hydroxyalkanoic acids and the corresponding 1,2-diols was studied. The addition reaction of tris(methylthio)methyllithium to the aldehydes (propanal–dodecanal) gave the corresponding 1,1,1-tris(methylthio)-2-alkanols <B>1a–j</B>. Treatment of <B>1</B> with mercury(II) chloride–mercury(II) oxide in water–acetone afforded <I>S</I>-methyl 2-hydroxyalkanethioates <B>2a–j</B>, and in methanol methyl 2-hydroxyalkanoates <B>3c–j</B> were obtained. Reduction of the thioates <B>2</B> with lithium aluminium hydride gave 1,2-diols <B>4c–j</B> and saponification produced the corresponding 2-hydroxyalkanoic acids <B>5c–j</B>.

• 公益社団法人 日本化学会の論文

著者

• Orito Kazuhiko

  Department of Chemical Process Engineering, Hokkaido University

関連論文

• Synthesis of S-methyl 2-hydroxyalkanethioates, 2-hydroxyalkanoic acids and related compounds via the addition reaction of tris(methylthio)methanide ion to alkanals.

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