This reaction was performed by Heath, Ronan, Francis, Nathan, Jonah, Oliver, Daniel, Stuart, Jacky and Erin.
3-(Trifluoromethyl)phenylacetonitrile (11.4g, 0.0617 mol) was added to ethyl propanoate (5.35 g, 0.0524 mol) and THF (100 mL). Potassium tert-butoxide (17.0 g, 0.152 mol) was added with stirring. The reaction mixture immediately turned red and warmed. The reaction was then placed in a water bath and the temperature maintained at 40°C with stirring for 7 h. The potassium tert-butoxide dissolved after 30 min of stirring.
HCl (80 mL, 1 M) was added to stop the reaction, then DCM (60 mL) was added. The intense red organic layer was collected, and the aqueous layer extracted with DCM (30 mL x 2). The organic layer was dried over sodium sulfate and then filtered.
A TLC was run in 25:75 EtOAc:hex, and showed that the crude mixture contains some starting material and two coloured spots. This is consistent with the expected keto and enol tautomers.