4-Iodophenylacetonitrile (250 mg, 1.03 mmol, 1 equiv.), ethyl propionate (102 mg, 0.876mmol, 1.1 equiv.) and potassium tert-butoxide (289 mg, 2.58 mmol, 2.5 equiv.) were combined in THF (2.5 mL) at room temperature, with stirring in a round bottom flask. The reaction mixture turned to a dark red and heated up rapidly.
The first reaction was conducted over a period of 16 hours with stirring. This resulted in a complex mixture of products according to TLC. The second run was only reacted for 4 hours with stirring for the first 30 min to limit the amount of dissolved oxygen introduced to the reaction system. This led to a clean crude TLC.
The reaction mixture was worked up by the addition of 1.0 M HCl (15 mL) to the reaction vessel. The acidified reaction mixture was transferred to a separating funnel and the aqueous layer was extracted with DCM (3 x 20 mL). The combined organic layer was washed with brine and dried with anhydrous sodium sulfate, filtered and concentrated in vacuo to afford a red oil. TLC analysis was conducted with 10:1 hexane : DCM as the eluent. TLC analysis indicated that the majority of the starting material had reacted.
NMR analysis revealed two main products. Out initial thinking is that the two products are the keto and enol forms of the reaction product according to characteristic peaks in the NMR spectra. Alternatively, the second product may be an oxygenated by-product due to the small scale of the reaction.