Synthesis
The general procedure for the synthesis of (Z)-3-iodoacrylic acid methyl ester from methyl propargylate was as follows: a mixed solution of methyl propargylate (15.0 g, 178 mmol) and lithium iodide (LiI, 26.3 g, 196 mmol) in acetic acid (178 mL) was heated with stirring at 70 °C. The reaction process was monitored by gas chromatography-mass spectrometry (GC-MS) (after neutralization). After 11 h of reaction, water (900 mL) was added to the reaction mixture and neutralized with solid potassium carbonate (K2CO3) until no carbon dioxide gas was produced. Subsequently, extraction was carried out with ether (1.8 L x 3). The organic phases were combined, dried over anhydrous sodium sulfate (Na2SO4) and concentrated under reduced pressure to give the crude product. The crude product was purified by silica gel column chromatography (petroleum ether/ethyl acetate = 30/1) to afford methyl (Z)-3-iodoacrylate (32.36 g, 89% yield) as a pale yellow oil.
References
[1] Journal of the American Chemical Society, 2004, vol. 126, # 32, p. 9926 - 9927
[2] Chemistry - A European Journal, 2014, vol. 20, # 28, p. 8594 - 8598
[3] Journal of Organic Chemistry, 2007, vol. 72, # 7, p. 2525 - 2532
[4] Tetrahedron, 2009, vol. 65, # 40, p. 8418 - 8427
[5] Angewandte Chemie - International Edition, 2015, vol. 54, # 34, p. 9958 - 9962
