2-Aminomethyl-1,1-diphenylbut-1-eneの合成について : 複素環式化合物の合成研究第239報

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Ethyl α-ethyl-β-hydroxy-β, β-diphenylpropionate (IV) was obtained in 71% yield from Reformatsky reaction between ethyl α-bromo-n-butyrate (III) and benzophenone. After the dehydration of IV with phosphorous oxychloride, the resulting ethyl α-ethyl-β, β-diphenylacrylate (VII) was hydrolized to give α-ethyl-β, β-diphenylacrylic acid (VIII), which was reacted to acid chloride with thionyl chloride in pyridine, and it was treated with ammonia giving α-ethyl-β, β-diphenylacrylamide (IX). IX was reduced with lithium aluminium hydride in dehydrated tetrahydrofuran to give 2-aminomethyl-1,1-diphenylbut-1-ene (I), which was confirmed as its hydrochloride. On the other hand, as abnormal products, 1,1-diphenylbut-1-ene (V), 2-ethyl-3-phenyliden-1-one (XIII) and XI were produced and they were confirmed by the elemental analyses and spectral data.
公益社団法人日本薬学会の論文
1968-07-25