Acetalation Mechanism of 2-Formyl-3-methoxypropionitrile in Methanolic Hydrogen Chloride

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概要

• 論文の詳細を見る

• 2-Dimethoxymethyl-3-methoxypropionitrile (I), an important compound for thiamine production, was obtained in good yield by the hydrogen chloride-catalyzed acetalation of 2-formyl-3-methoxypropionitrile (II) in methanol. The reaction was proved not to proceed through direct acetalation of the formyl group but via the pathway of II→allyl hydroxy-(V) and allyl ether-(VI) cations→2-dimethoxymethylacrylonitrile (III)⇌2-methoxymethylene-3-methoxypropionitrile (IV)⇌I. The reaction gave 2-oxopiperidines (VII, VIII) and pyrans (IX, X) as minor products which should be formed by the attack of the allyl cations to II or IV. Kinetic studies on the reaction pathway of III⇌IV⇌I revealed that the cis isomer of IV was more reactive than the trans counterpart. The same acetalation of methyl 2-formyl-3-methoxypropionate (XVI) was similarly investigated.

• 公益社団法人日本薬学会の論文
• 1978-01-25

著者

• 田中 守

  Production Department Shionogi And Co. Ltd.

• 徳山 幹治

  Production Department, Shionogi and Co., Ltd.

• 木本 みつる

  Production Department, Shionogi and Co., Ltd.

• 徳山 幹治

  Production Department Shionogi And Co. Ltd.

• 木本 みつる

  Production Department Shionogi And Co. Ltd.

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• Acetalation Mechanism of 2-Formyl-3-methoxypropionitrile in Methanolic Hydrogen Chloride
• Polysaccharides in Lichens and Fungi. I. Antitumour Active Polysaccharides of Gyrophora esculenta MIYOSHI and Lasallia papulosa (ACH.) LANO

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