Efficient and scalable synthesis of 3-(polyfluoroacyl)pyruvaldehydes dimethyl acetals: A novel functionalized fluorinated building-block | Health & Environmental Research Online (HERO)

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Citation
Tags

HERO ID

3860754

Reference Type

Journal Article

Title

Efficient and scalable synthesis of 3-(polyfluoroacyl)pyruvaldehydes dimethyl acetals: A novel functionalized fluorinated building-block

Author(s)

Chizhov, DL; Belyaev, DV; Yachevskii, DS; Rusinov, GL; Chupakhin, ON; Charushin, VN

Year

2017

Is Peer Reviewed?

Yes

Journal

Journal of Fluorine Chemistry
ISSN: 0022-1139
EISSN: 1873-3328

Volume

199

Page Numbers

39-45

DOI

10.1016/j.jfluchem.2017.04.009

Web of Science Id

WOS:000404204300006

Abstract

An efficient approach for the synthesis of 3-(polyfluoroacyl)pyruvaldehydes dimethyl acetals (1,1-dimethoxy-4polyfluoroalkyl-butan-2,4-dions) from 1,1-dimethoxyacetone and polyfluorinated carboxylic acid esters has been developed. The procedure includes the Claisen type condensation of the starting materials by means of calcium hydride in methanol, followed by isolation of copper complexes of the corresponding diketones and their destroying with disodium EDTA. A simple synthesis of 5(3)-(polyfluoroalkyl)-1H-pyrazole-3(5)-carbaldehydes and their acetals is also presented.

Keywords

Fluorinated 1,3-diketones; Acetals; Claisen condensation; Calcium hydride; 3-(Polyfluoracyl)pyruvaldehydes; Pyrazole-1H-3-carbaldehydes