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Title: Scalable Preparation of the Masked Acyl Cyanide TBS-MAC
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.).  more » « less
Award ID(s):
1848257
PAR ID:
10502893
Author(s) / Creator(s):
; ; ; ;
Publisher / Repository:
MDPI
Date Published:
Journal Name:
Molecules
Volume:
28
Issue:
13
ISSN:
1420-3049
Page Range / eLocation ID:
5087
Subject(s) / Keyword(s):
masked acyl cyanide MAC umpolung synthon synthetic equivalent scalable
Format(s):
Medium: X
Sponsoring Org:
National Science Foundation
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