%0 Journal Article
%T Scalable Preparation of the Masked Acyl Cyanide TBS-MAC.
%A Hinton H
%A Patterson J
%A Hume J
%A Patel K
%A Pigza J
%J Molecules
%V 28
%N 13
%D 2023 Jun 29
%M 37446749
%F 4.927
%R 10.3390/molecules28135087
%X 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.).