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.

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Publication Details

Journal
SynOpen
Published
2024-12-20
DOI
https://doi.org/10.1055/a-2507-3829
Citations
1
Primary Topic
Phosphorus compounds and reactions
Type
article
Field-Weighted Citation Impact
0.25
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article

Development of a Novel Horner–Wadsworth–Emmons Reagent for the Facile Preparation of Mixed Phosphonoacetates

Shigeki Sano, Masaru Okamoto, Syuji Kitaike, Akira Imai et al.
1 citations
SynOpen
Phosphorus compounds and reactions
0.25
article

Development of a Novel Horner–Wadsworth–Emmons Reagent for the Facile Preparation of Mixed Phosphonoacetates

Shigeki Sano, Masaru Okamoto, Syuji Kitaike, Akira Imai, Michiyasu Nakao, Satoshi Isetani
article en
1 citations

Abstract

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.

SynOpenVol. 09(01)
Tokushima University (JP)
Clean water and sanitation
Openalex Percentile: Top 45%
Phosphorus compounds and reactions
0.25
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