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DOI: 10.1055/a-2507-3829
Development of a Novel Horner–Wadsworth–Emmons Reagent for the Facile Preparation of Mixed Phosphonoacetates
Abstract
A novel Horner–Wadsworth–Emmons (HWE) reagent, methyl 2-[bis(3,4,5-trifluorophenoxy)phosphoryl]acetate, was synthesized by the reaction of methyl 2-(dichlorophosphoryl)acetate and 3,4,5-trifluorophenol. Sequential alcoholysis of this HWE reagent with isopropyl alcohol and benzyl alcohol on the phosphorus atom afforded the mixed phosphonoacetate, methyl 2-[(benzyloxy)(isopropoxy)phosphoryl]acetate, in 89% yield for the two steps.
Key words
Horner–Wadsworth–Emmons reagents - methyl 2-[bis(3,4,5-trifluorophenoxy)phosphoryl]acetate - alcoholysis - fluorophenols - mixed phosphonoacetates - phosphorus–sulfur bonds - phosphonothioateSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-2507-3829.
- Supporting Information
Publication History
Received: 20 November 2024
Accepted after revision: 18 December 2024
Accepted Manuscript online:
20 December 2024
Article published online:
05 March 2025
© 2025. The Author(s). This is an open access article published by Thieme under the terms of the Creative Commons Attribution License, permitting copying and reproduction so long as the original work is given appropriate credit. Contents may not be used for commercial purposes or adapted, remixed, transformed or built upon. (https://creativecommons.org/licenses/by/4.0/)
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