25491-79-6Relevant academic research and scientific papers
FLUORINATED 3-DIETHYLAMINOPROPENOATES AND THEIR REACTIONS
Svoboda, Jiri,Paleta, Oldrich,Liska, Frantisek,Dedek, Vaclav
, p. 1389 - 1396 (2007/10/02)
The reaction of diethylamine with methyl trifluoropropenoate (I), methyl 2-chloro-3,3-difluoropropenoate (II), methyl 3,3-difluoropropenoate (III) and methyl 3-chloro-2,3-difluoropropenoate (IV) affords halogenated 3-diethylaminopropenoates V-VII via the vinylic substitution of fluorine or chlorine atoms.When hydrolyzed the latter give methyl N,N-diethylcarbamoylacetates X-XII.On addition of 1-butanol and 2,2,3,3-tetrafluoropropanol to aminopropenoates V-VII fluorinated 3-alkoxy-3-diethylaminopropenoates XIII-XVI were prepared which when hydrolyzed eliminate thediethylamino group under formation of alkyl methylpropanedioates XX to XXIII.Heating of aminoethers XIII-XVI at 150 deg C gives 1-fluorobutane or 1,1,2,2,3-pentafluoropropane, respectively.These fluoro derivatives are also formed on heating of the mentioned alcohols with 3-diethylaminopropenoates V-VII.During the thermal decomposition of methyl 2-chloro-3-diethylamino-3-fluoro-3-(2,2,3,3-tetrafluoropropoxy)propanoate (XV) 3-chloro-1,1,2,2-tetrafluoropropane was formed as a by-product.The substitution of the hydroxyl group with fluorine is discussed from the point of view of preparative application.
