This paper describes the three-step synthesis of TBS-MAC, a masked acyl cyanide (MAC) and a versatile one-carbon oxidation state three synthon. We have developed a scalable and detailed synthesis that involves: (1) acetylation of malononitrile to form the sodium enolate, (2) protonation of the enolate to form acetylmalononitrile, and (3) epoxidation of the enol, rearrangement to an unstable alcohol, and TBS-protection to form the title compound. Both the sodium enolate and acetylmalononitrile are bench-stable precursors to the intermediate hydroxymalononitrile, which can be converted to other MAC reagents beyond TBS by varying the protecting group (Ac, MOM, EE, etc.).

中文翻译：

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掩蔽酰基氰化物 TBS-MAC 的规模化制备

本文描述了 TBS-MAC、掩蔽酰基氰化物 (MAC) 和多功能一碳氧化态三合成子的三步合成。我们开发了一种可扩展且详细的合成方法，包括：（1）丙二腈乙酰化形成烯醇钠，（2）烯醇化物质子化形成乙酰丙二腈，（3）烯醇环氧化，重排成不稳定的醇，以及TBS-保护形成标题化合物。烯醇钠和乙酰基丙二腈都是中间体羟基丙二腈的实验室稳定前体，可以通过改变保护基（Ac、MOM、EE 等）将其转化为 TBS 之外的其他 MAC 试剂。