A practical process for the preparation of bis(2,2,2-trifluoroethyl) 2-oxoalkylphosphonates by acylation with carboxylic esters

Katalin Molnár, László Takács, Mihály Kádár, F. Faigl, Zsuzsanna Kardos

Research output: Contribution to journalArticle

6 Citations (Scopus)

Abstract

The preparation of bis(2,2,2-trifluoroethyl) 2-oxoalkylphosphonates by the acylation of bis(2,2,2-trifluoroethyl) methylphosphonate was re-investigated using esters rather than the sensitive acyl chlorides. Based on our optimization, the best results were achieved when the base (LiHMDS) was added to a solution of the phosphonate and the acylating agent at -90°C.

Original languageEnglish
Pages (from-to)4877-4879
Number of pages3
JournalTetrahedron Letters
Volume56
Issue number34
DOIs
Publication statusPublished - Mar 24 2015

Fingerprint

Acylation
Organophosphonates
Chlorides
Esters
methylphosphonic acid

Keywords

  • Acylation
  • Bis(trifluoroethyl) 2-oxoalkylphosphonate
  • Carboxylic ester
  • Horner-Wadsworth-Emmons reaction
  • Oxo-phosphonate
  • Trifluoroethyl phosphonate

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

A practical process for the preparation of bis(2,2,2-trifluoroethyl) 2-oxoalkylphosphonates by acylation with carboxylic esters. / Molnár, Katalin; Takács, László; Kádár, Mihály; Faigl, F.; Kardos, Zsuzsanna.

In: Tetrahedron Letters, Vol. 56, No. 34, 24.03.2015, p. 4877-4879.

Research output: Contribution to journalArticle

Molnár, Katalin ; Takács, László ; Kádár, Mihály ; Faigl, F. ; Kardos, Zsuzsanna. / A practical process for the preparation of bis(2,2,2-trifluoroethyl) 2-oxoalkylphosphonates by acylation with carboxylic esters. In: Tetrahedron Letters. 2015 ; Vol. 56, No. 34. pp. 4877-4879.
@article{d4e91b3ac8f0443baa5423c77497c728,
title = "A practical process for the preparation of bis(2,2,2-trifluoroethyl) 2-oxoalkylphosphonates by acylation with carboxylic esters",
abstract = "The preparation of bis(2,2,2-trifluoroethyl) 2-oxoalkylphosphonates by the acylation of bis(2,2,2-trifluoroethyl) methylphosphonate was re-investigated using esters rather than the sensitive acyl chlorides. Based on our optimization, the best results were achieved when the base (LiHMDS) was added to a solution of the phosphonate and the acylating agent at -90°C.",
keywords = "Acylation, Bis(trifluoroethyl) 2-oxoalkylphosphonate, Carboxylic ester, Horner-Wadsworth-Emmons reaction, Oxo-phosphonate, Trifluoroethyl phosphonate",
author = "Katalin Moln{\'a}r and L{\'a}szl{\'o} Tak{\'a}cs and Mih{\'a}ly K{\'a}d{\'a}r and F. Faigl and Zsuzsanna Kardos",
year = "2015",
month = "3",
day = "24",
doi = "10.1016/j.tetlet.2015.06.068",
language = "English",
volume = "56",
pages = "4877--4879",
journal = "Tetrahedron Letters",
issn = "0040-4039",
publisher = "Elsevier Limited",
number = "34",

}

TY - JOUR

T1 - A practical process for the preparation of bis(2,2,2-trifluoroethyl) 2-oxoalkylphosphonates by acylation with carboxylic esters

AU - Molnár, Katalin

AU - Takács, László

AU - Kádár, Mihály

AU - Faigl, F.

AU - Kardos, Zsuzsanna

PY - 2015/3/24

Y1 - 2015/3/24

N2 - The preparation of bis(2,2,2-trifluoroethyl) 2-oxoalkylphosphonates by the acylation of bis(2,2,2-trifluoroethyl) methylphosphonate was re-investigated using esters rather than the sensitive acyl chlorides. Based on our optimization, the best results were achieved when the base (LiHMDS) was added to a solution of the phosphonate and the acylating agent at -90°C.

AB - The preparation of bis(2,2,2-trifluoroethyl) 2-oxoalkylphosphonates by the acylation of bis(2,2,2-trifluoroethyl) methylphosphonate was re-investigated using esters rather than the sensitive acyl chlorides. Based on our optimization, the best results were achieved when the base (LiHMDS) was added to a solution of the phosphonate and the acylating agent at -90°C.

KW - Acylation

KW - Bis(trifluoroethyl) 2-oxoalkylphosphonate

KW - Carboxylic ester

KW - Horner-Wadsworth-Emmons reaction

KW - Oxo-phosphonate

KW - Trifluoroethyl phosphonate

UR - http://www.scopus.com/inward/record.url?scp=84937635403&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=84937635403&partnerID=8YFLogxK

U2 - 10.1016/j.tetlet.2015.06.068

DO - 10.1016/j.tetlet.2015.06.068

M3 - Article

AN - SCOPUS:84937635403

VL - 56

SP - 4877

EP - 4879

JO - Tetrahedron Letters

JF - Tetrahedron Letters

SN - 0040-4039

IS - 34

ER -