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3rd June 2018 @ 23:06

Reaction performed by Heath, Jonah, Ronan, Francis, Stuart, Daniel, Oliver, Jacky, Nathan and Erin!

SGS18-2-1

4-(trifluoromethyl)phenylacetonitrile (10 g, 0.054 mol) was added to ethyl propanoate (5.52 g, 0.055 mol) and THF (100 mL), and stirred until dissolved. Potassium tert-butoxide (12.5 g, 0.112 mol) was added with stirring.  The reaction immediately turned red and warmed to ~40 oC.  The reaction was kept at this temperature and stirred for 7 h.

HCl (80 mL, 1 M) was added to stop the reaction, then DCM (40 mL) was added. The intense red organic layer was collected, and the aqueous layer extracted with DCM (20 mL x 2). The organic layer was dried over sodium sulfate and then filtered.

TLCs were run in 10:90 EtOAc:hex and 25:75 EtOAc:hex, and both showed that the crude mixture contains some starting material and two coloured spots.  This is consistent with the expected keto and enol tautomers. 

After addition of potassium tert-butoxide