Selective protection of carbonyl groups by taking advantage of a combination of solid support and Girard's reagent.
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概要
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Some Girard's derivatives of 4-phenylbenzophenone were prepared in ethanol solution, in the presence of Amberlite IRC-50 as a catalyst. Supported samples of the derivatives were then prepared by addition of silica gel to the solution, followed by evaporation of the ethanol. The supported samples were reduced with lithium tri-<I>t</I>-butoxyhydroaluminate by being suspended in THF solution. Hydrolysis, followed by extraction of the product, yielded 4-acetyl-α-phenylbenzyl alcohol in an 80% selectivity. In the same way, 4-acetylbenzaldehyde yielded 1-(4-formylphenyl)ethanol in an 81% selectivity. Relatively unhindered carbonyl groups were preferentially protected. Utilization of Girard's reagents was successfully made as a protecting reagent and also as an extracting reagent of carbonyl compounds.
- 公益社団法人 日本化学会の論文
著者
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Chihara Teiji
The Institute of Physical and Chemical Research
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Taya Kazuo
Department of Chemistry, Tokyo Gakugei University
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Waniguchi Erika
Department of Chemistry, Tokyo Gakugei University
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Wakabayashi Tamie
Department of Chemistry, Tokyo Gakugei University
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