Application
(1-Methyl-1H-imidazol-4-yl)methanol is an organic intermediate that can be obtained by reducing 1-methyl-imidazol-4-carboxylic acid. It can be further chlorinated to prepare 1-methyl-4-chloromethylimidazolium hydrochloride. As an organic synthesis intermediate and pharmaceutical intermediate, it can be used in laboratory research and development processes and chemical production processes.
Synthesis
General procedure for the synthesis of (1-methyl-1H-imidazol-4-yl)methanol from 1-methyl-1H-imidazole-4-carboxylic acid: 1-methyl-1H-imidazole-4-carboxylic acid (25 g, 198 mmol) was dissolved in tetrahydrofuran (THF) (1000 mL) under nitrogen protection. Lithium aluminum hydride (LiAlH4) (15.05 g, 396 mmol) was added slowly at room temperature. The reaction mixture was stirred at 50 °C for 12 hours. Upon completion of the reaction, water (15 mL), 10% sodium hydroxide solution (15 mL), and water (45 mL) were sequentially added to the reaction mixture at 0 °C. The solid was removed by filtration and the filtrate was concentrated to afford the target product (1-methyl-1H-imidazol-4-yl)methanol (13.2 g, 94 mmol, 47.5% yield), which could be used in the next step of the reaction without further purification.LC-MS analysis result: m/z 113.1 ([M + H]+), retention time 0.33 min.
References
[1] Patent: WO2004/13134, 2004, A2. Location in patent: Page 26
[2] Patent: WO2004/13135, 2004, A1. Location in patent: Page 47
[3] Patent: WO2004/16606, 2004, A1. Location in patent: Page 30
[4] Patent: WO2004/13138, 2004, A2. Location in patent: Page 23
[5] Patent: WO2017/60854, 2017, A1. Location in patent: Page/Page column 474; 475
