Synthesis
The general procedure for the synthesis of 1-methyl-2-hydroxymethyl-1H-imidazole is as follows: synthesis of (1-methyl-1H-imidazol-2-yl)methanol (BB6): to a solution of 1-methyl-1H-imidazole-2-carboxaldehyde (BB5) (40.5 g, 368 mmol) in methanol (300 mL) was added sodium borohydride (NaBH4) (20.89 g) in batches at 0 °C. . The reaction mixture was slowly warmed to room temperature and stirred for 5 hours. Upon completion of the reaction, the mixture was cooled to 0 °C, water (150 mL) was added and stirring was continued at 0 °C for 30 min. Subsequently, the mixture was concentrated under vacuum at room temperature. The crude product was dissolved in water (150 mL) and extracted with chloroform (4 x 200 mL). The organic layers were combined, dried over anhydrous sodium sulfate (Na2SO4) and concentrated. The residue was stirred with ether (Et2O, 150 mL) and filtered to give a white solid product (BB6) (36 g, 87% yield). Thin layer chromatography (TLC) showed an Rf value of 0.4 (15% methanol/chloroform spread).1H NMR (400 MHz, CDCl3) data: δ 6.89 (1H, apparent double peaks), 6.83 (1H, apparent double peaks), 4.66 (2H, single peak), 3.72 (3H, single peak); Mass Spectrometry (m/z): 113 (MH)+.
References
[1] Tetrahedron, 2000, vol. 56, # 4, p. 645 - 657
[2] Patent: US2012/322722, 2012, A1
[3] Bioorganic and Medicinal Chemistry, 2005, vol. 13, # 2, p. 363 - 386
[4] Tetrahedron, 1996, vol. 52, # 48, p. 15171 - 15188
[5] South African Journal of Chemistry, 2012, vol. 65, p. 231 - 238
