Synthesis
General procedure for the synthesis of (1H-imidazol-2-yl)-methanol from 1H-imidazole-2-carboxaldehyde: A solution of 1H-imidazole-2-carboxaldehyde (5 g, 52.08 mmol) in methanol (50 mL) was added to a 500 mL round-bottomed flask, and the ice bath was cooled to 0 °C. Sodium borohydride (3.93 g, 104.16 mmol) was added in batches with stirring, removed from the ice bath after addition, and the reaction mixture was allowed to stir at room temperature for 3 hours. Upon completion of the reaction, the reaction was quenched with saturated sodium chloride solution (25 mL) and subsequently concentrated under reduced pressure in a rotary evaporator to remove most of the solvent. The crude product was purified by silica gel column chromatography with 10% methanol/chloroform (v/v) as eluent to afford (1H-imidazol-2-yl)-methanol as a light yellow solid (4 g, 78% yield). Thin layer chromatography (TLC) showed an Rf value of 0.1 (unfolding agent: 10% methanol/chloroform).1H NMR (400 MHz, CD3OD) δ: 6.97 (s, 2H), 4.61 (s, 2H).
References
[1] Bioorganic and Medicinal Chemistry Letters, 2013, vol. 23, # 3, p. 827 - 833
[2] Patent: WO2015/36759, 2015, A1. Location in patent: Page/Page column 200
[3] Journal of Organic Chemistry, 2010, vol. 75, # 10, p. 3208 - 3213
[4] Bioorganic and Medicinal Chemistry Letters, 2011, vol. 21, # 19, p. 5849 - 5853
[5] Patent: US9138427, 2015, B2. Location in patent: Page/Page column 302
