Efficient and scalable synthesis of 3-(polyfluoroacyl)pyruvaldehydes dimethyl acetals: A novel functionalized fluorinated building-block / Chizhov Dmitrii L.,Belyaev Danila V.,Yachevskii Danil S.,Rusinov Gennady L.,Chupakhin Oleg N.,Charushin Valery N. // JOURNAL OF FLUORINE CHEMISTRY. - 2017. - V. 199, l. . - P. 39-45.

ISSN/EISSN:

0022-1139 / 1873-3328

Type:

Article

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.

Author keywords:

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

DOI:

10.1016/j.jfluchem.2017.04.009

Web of Science ID:

ISI:000404204300006

Соавторы в МНС:

Другие поля

Поле	Значение
Month	JUL
Publisher	ELSEVIER SCIENCE SA
Address	PO BOX 564, 1001 LAUSANNE, SWITZERLAND
Language	English
EISSN	1873-3328
Keywords-Plus	REGIOSELECTIVE SYNTHESIS; HETEROCYCLES
Research-Areas	Chemistry
Web-of-Science-Categories	Chemistry, Inorganic \& Nuclear; Chemistry, Organic
Author-Email	dlchizhov@ios.uran.ru
Funding-Acknowledgement	Program for the Support of Leading Scientific School {[}8922.2016.3]; Program of the Ural Division of the RAS {[}15-21-37]
Funding-Text	This research was financially supported by the Program for the Support of Leading Scientific School (grant No. 8922.2016.3) and the Program of the Ural Division of the RAS (No. 15-21-37). Spectroscopic investigations and elemental analysis have been made in the Institute of Organic Synthesis, Ural Division of the RAS, Ekaterinburg, Russia
Number-of-Cited-References	26
Usage-Count-Last-180-days	6
Usage-Count-Since-2013	6
Journal-ISO	J. Fluor. Chem.
Doc-Delivery-Number	EY7XA