Synthesis
A solution of anhydrous THF (20 mL) of ethyl 2-(1-imidazolyl)acetate (6.05 g, 39.2 mmol) was added dropwise to a mixture of lithium aluminum hydride (3.00 g, 79.1 mmol) and anhydrous THF (60 mL) at 0 °C under a dry argon atmosphere. The reaction mixture was stirred at 0 °C for 5 minutes, followed by continued stirring at room temperature for 4 hours. Upon completion of the reaction, water (3 mL), 15% aqueous sodium hydroxide solution (3 mL) and water (9 mL) were added sequentially and dropwise at 0 °C to quench the reaction. The resulting mixture was stirred at room temperature for 12 hours and then filtered. The filtrate was concentrated under reduced pressure and the residue was purified by silica gel column chromatography using chloroform/methanol (10:1, v/v) as eluent. The grades with an Rf value of 0.22 were collected and further purified twice by decompression distillation to finally obtain 1-(2-hydroxyethyl)imidazole (Im2OH) as a colorless oil (2.386 g, 54% yield).
References
[1] Medicinal Chemistry, 2012, vol. 8, # 5, p. 865 - 873
[2] Journal of Medicinal Chemistry, 1996, vol. 39, # 10, p. 1991 - 2007
[3] Journal of Medicinal Chemistry, 2018, vol. 61, # 6, p. 2604 - 2610
[4] Reactive and Functional Polymers, 2016, vol. 99, p. 1 - 8
[5] European Journal of Medicinal Chemistry, 2009, vol. 44, # 8, p. 3350 - 3355
