Potassium Carbonate → HCID 15013402, compound

Participants

Reaction Steps

3.65 g of p-iodobenzonitrile, 6.25 g of ethyl propiolate, 220 mg of dichlorobis(triphenylphosphine)palladium, 120 mg CuI, and 4.42 g potassium carbonate were combined in a round-bottom flask along with 50 mL freshly distilled THF. This mixture was refluxed while magnetically stirring for 4 hrs. THF was then removed in vacuo. The reaction mixture was extracted with CH2Cl2 (2×150 mL). The combined organic layers were washed with H2O (2×100 mL) and brine (1×100 mL), dried over MgSO4, and concentrated to give a brown/black oily solid as a crude product. Purification by automated flash chromatography (silica gel, ethyl acetate/hexanes) gave the intermediate product ethyl (4-cyano)phenylpropiolate as a white solid in 45% yield. This intermediate product was analyzed by 1HNMR (CDCl3) δ1.36 (t, 3 H, J=7.2 Hz), 4.31 (q, 2 H, J=7.2 Hz), 7.67 (s, 4 H).

Provenance & Evidence