{Reference Type}: Journal Article
{Title}: Scalable Preparation of the Masked Acyl Cyanide TBS-MAC.
{Author}: Hinton H;Patterson J;Hume J;Patel K;Pigza J;
{Journal}: Molecules
{Volume}: 28
{Issue}: 13
{Year}: 2023 Jun 29
{Factor}: 4.927
{DOI}: 10.3390/molecules28135087
{Abstract}: 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.).