Synthesis
Meldrum acid (2.00 g, 13.8 mmol) and anhydrous acetonitrile (40 mL) were added to a flame-dried 150 mL pressure tube under argon protection. Benzyl alcohol (1.44 mL, 13.8 mmol) was added to the resulting solution and the reaction tube was sealed. The reaction mixture was refluxed overnight. Upon completion of the reaction, the solvent was removed by concentration under reduced pressure and the product was purified by column chromatography (eluent: 70/30 hexane/ethyl acetate) to afford the target product, monophenylmethyl malonate (1.28 g, 6.59 mmol), as a colorless oil in 48% yield.
References
[1] Helvetica Chimica Acta, 2002, vol. 85, # 1, p. 288 - 319
[2] Heterocycles, 1993, vol. 35, # 2, p. 1205 - 1235
[3] Bioorganic and Medicinal Chemistry, 2010, vol. 18, # 3, p. 1143 - 1148
[4] Journal of Organometallic Chemistry, 2001, vol. 619, # 1-2, p. 179 - 193
[5] Bioorganic and Medicinal Chemistry Letters, 2015, vol. 25, # 21, p. 4933 - 4936
