US 7,488,828 B2
Process for the preparation of 4-trifluoromethyl-2(1H)-pyridinone
Christopher Thomas Hamilton, Midland, Mich. (US); Michael Frederick Gullo, Midland, Mich. (US); Michael Allen Gonzalez, Sanford, Mich. (US); Gary Alan Roth, Midland, Mich. (US); David Bruce Gorman, Midland, Mich. (US); Joachim Gebhardt, Wachenheim (Germany); Norbert Götz, Worms (Germany); Hagen Jaedicke, Ludwigshafen (Germany); Guido Mayer, Gönnheim (Germany); and Michael Rack, Heidelberg (Germany)
Assigned to Dow AgroSciences LLC, Indianapolis, Ind. (US)
Filed on Jun. 24, 2005, as Appl. No. 11/166,485.
Prior Publication US 2005/0288511 A1, Dec. 29, 2005
Int. Cl. C07D 211/72 (2006.01)
U.S. Cl. 546—290  [546/303] 6 Claims
 
1. A process for the preparation of 4-trifluoromethyl-2(1H)-pyridinone (I),

OG Complex Work Unit Drawing
which comprises:
i) contacting either a 4-alkoxy-1,1,1-trifluorobut-3-en-2-one of the formula

OG Complex Work Unit Drawing
in which R represents C1-C4 alkyl, or a 4,4-dialkoxy-1,1,1-trifluorobutan-2-one of the formula

OG Complex Work Unit Drawing
in which R is as previously defined, with a trialkyl phosphonoacetate of the formula:

OG Complex Work Unit Drawing
in which R is as previously defined, in the presence of a base and an alcohol or glycol solvent to provide a mixture of condensation products of the formula

OG Complex Work Unit Drawing
in which R is as previously defined;
and
ii) cyclizing the mixture of condensation products to provide 4-trifluoromethyl-2(1H)-pyridinone.