Synthesis
Under nitrogen protection, 1H-imidazole (40.8 g, 600.00 mmol) was dissolved in ethanol (1200 mL), followed by addition of a tetrahydrofuran (1200 mL) solution of sodium ethanolate (40.8 g, 600.00 mmol). The reaction mixture was stirred at room temperature for 1 hour and then concentrated under vacuum. To the concentrated residue was added chloromethyl methyl ether (53.4 g, 667.50 mmol) and the resulting solution was stirred at room temperature overnight. After completion of the reaction, the solid impurities were removed by filtration. The filtrate was concentrated and purified by distillation under reduced pressure to give 40 g (58% yield) of 1-(methoxymethyl)imidazole as a white oil.
References
[1] European Journal of Organic Chemistry, 2011, # 24, p. 4654 - 4666
[2] Chemical Communications, 2017, vol. 53, # 82, p. 11302 - 11305
[3] Patent: WO2009/139834, 2009, A1. Location in patent: Page/Page column 142-143
[4] Journal of Organic Chemistry, 1989, vol. 54, # 6, p. 1439 - 1442
[5] Journal of Medicinal Chemistry, 1997, vol. 40, # 2, p. 216 - 225
