著者

鈴木 洸次郎 谷相 美智 毛利 智代 藤山 亮治 清岡 俊一

出版者

公益社団法人 日本化学会

雑誌

日本化学会誌(化学と工業化学) (ISSN:03694577)

巻号頁・発行日

vol.1987, no.2, pp.257-259, 1987-02-10 (Released:2011-05-30)

参考文献数

9

被引用文献数

2

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exo-3-Formy1-3-methylcamphor was synthesized by a following route, for the purpose of asymmetric alkylation of glycine.Methyl 3-methyl-3-camphorca rboxylates [4] were obtained by the methylation of methyl 3-camphorcarboxylate [3] with sodium hydride and methyl iodide in good yield. The products were separated into two parts by treating with ligroine, i. e. a crystalline part [4a](mp 88-48.5°C) and an oily one [4b]. It was found that the structure of [4a] was determined as exo-3-carboxylate and that of [4b] was as endo-one by the analyses of their NMR data. The reduction of [4a] with LiAlH4 gave diol[5] And exo-3-formy1-3-methylcampho r was obtained as a slightly unstable liquid (bp 123°C/13 mmHg, [α]D20 162.5°) by the oxida-tion of [5] with Collins' reagent.