Synthesis
Synthesis procedure for tert-butyl 3-hydroxypent-4-enoate (16): n-butyllithium (1.6 M in hexane, 68.8 mL, 110.0 mmol, 1.1 eq.) was added slowly and dropwise to an anhydrous THF (0.2 M) solution of diisopropylamine (11.0 g, 110.0 mmol, 1.1 eq.) at 0 °C. The reaction mixture was stirred at 0 °C for 60 min and then cooled to -78 °C. Subsequently, tert-butyl acetate (11.6 g, 100.0 mmol, 1.0 eq.) was added and stirring was continued at -78 °C for 2 hours. Next, freshly distilled acrolein (5.6 g, 100.0 mmol, 1.0 eq.) was added dropwise and the reaction mixture was warmed to room temperature and stirring was continued for 3 hours. Upon completion of the reaction, distilled water was added for hydrolysis and then extracted with ethyl acetate. The organic layers were combined, dried with anhydrous magnesium sulfate and concentrated under reduced pressure. Finally, the target product tert-butyl 3-hydroxypent-4-enoate (16.2 g, 84 mmol, 94%) was purified by silica gel column chromatography using hexane/ethyl acetate (5:1) as eluent to afford the target product as a colorless oil.
References
[1] Organic letters, 2002, vol. 4, # 13, p. 2205 - 2208
[2] Journal of Medicinal Chemistry, 2010, vol. 53, # 12, p. 4654 - 4667
[3] Beilstein Journal of Organic Chemistry, 2014, vol. 10, p. 1796 - 1801
[4] European Journal of Organic Chemistry, 2016, vol. 2016, # 2, p. 252 - 254
[5] Tetrahedron Letters, 2009, vol. 50, # 13, p. 1416 - 1418
