The Rupe Rearrangement: A New Efficient Method for Large-Scale Synthesis of Unsaturated Ketones in the Pilot Plant

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• 作者：Hilmar Weinmann ; Michael Harre ; Harribert Neh ; Klaus Nickisch ; Carlo Skö ; tsch ; and Ulf Tilstam
• 刊名：Organic Process Research & Development
• 出版年：2002
• 出版时间：May 2002
• 年：2002
• 卷：6
• 期：3
• 页码：216 - 219
• 全文大小：45K
• 年卷期：v.6,no.3(May 2002)
• ISSN：1520-586X

文摘

During scale-up studies of a new steroidal drug, the Ruperearrangement of an intermediate was investigated in detail.As the traditional method for this reaction was not adaptablesafely to conditions for the pilot plant, a new procedure had tobe developed. It was found that the reaction can be catalyzedby strongly acidic cation-exchange resins in a very economicalway. The yield of the reaction product was dramaticallyincreased compared to that in the original method. From anenvironmental point of view, this method is also superior totraditional approaches as catalyst and solvent can be recycledand the waste streams are greatly reduced. The reaction wasrun successfully on a scale of 64 kg in the pilot plant.Furthermore, the procedure was applied successfully to severalother steroids on a laboratory scale.