Document Type
Article
Publication Date
6-29-2023
Department
Chemistry and Biochemistry
School
Mathematics and Natural Sciences
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.).
Publication Title
Molecules
Volume
28
Issue
13
Recommended Citation
Hinton, H.,
Patterson, J.,
Hume, J.,
Patel, K.,
Pigza, J.
(2023). Scalable Preparation of the Masked Acyl Cyanide TBS-MAC. Molecules, 28(13).
Available at: https://aquila.usm.edu/fac_pubs/21350