The regioselective C-hydroxyalkylation of 1,3-diphenyl-1,3-propanedione with halo alcohols, involving intramolecular alcoholysis: the synthesis of oxoalkyl esters.
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概要
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The reaction of 1,3-diphenyl-1,3-propanedione (<B>1</B>) with 2-chloroethanol (<B>2</B>) or 3-chloro-1-propanol (<B>3</B>) was performed in the presence of potassium carbonate and sodium iodide as an improved procedure for regioselective <I>C</I>-hydroxyalkylation, involving intramolecular alcoholysis; the effects of the solvents, the temperature, and the amounts of potassium carbonate and sodium iodide were also investigated. The reaction with <B>2</B> afforded 3-benzoylpropyl benzoate (<B>4</B>) (<I>ca.</I> 70% yield), together with 2-benzoylmethyl-2-phenyl-1,3-dioxolane (<B>5</B>) (<I>ca.</I> 15% yield). The reaction with <B>3</B>, on the other hand, gave 4-benzoylbutyl benzoate (92–94% yield); the corresponding 1,3-dioxane derivative was detected only in a trace. Moreover, the reaction of <B>1</B> with 2-hydroxyethyl tosylate was similarly performed, but the yields of both <B>4</B> and <B>5</B> were unexpectedly low.
- 公益社団法人 日本化学会の論文
著者
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Ishido Yoshiharu
Department Of Chemistry Tokyo Institute Of Technology
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Inoue Kimio
Department of Chemistry, Faculty of Science, Tokyo Institute of Technology
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Tsutsumi Hideo
Department of Chemistry, Faculty of Science, Tokyo Institute of Technology
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