Methanesulfonic Acid → HCID 178440108, compound

Participants

Reaction Steps

A solution of 4-chloro-2-(1-methylethyl)-5-{[(phenylmethyl)oxy]methyl}-1H-imidazole (0.710 g, 2.7 mmol) and methanesulfonic acid (6.8 mL, 105 mmol) in chloroform (14 mL) was stirred at RT for 1 h. The reaction mixture was poured into ice (˜50 g) and the solution was neutralized by addition of 5N NaOH until the pH was 10. The solution was extracted with methyl tert-butyl ether (2×40 mL) followed by n-butanol (3×20 mL). The combined n-butanol extracts were concentrated, azeotroped with toluene, and dried in vacuo to provide crude [4-chloro-2-(1-methylethyl)-1H-imidazol-5-yl]nethanol as a brown solid. A solution of this solid and manganese dioxide (1.5 g, 17.0 mmol) in CH2Cl2 (8 mL) and 1,4-dioxane (4 mL) was heated under reflux for 6 h. The reaction mixture was cooled to RT and filtered through celite, and washed thoroughly with CH2Cl2. The filtrate was concentrated and dried to provide the title compound (0.165 g, 37%) as an off-white solid. 1H NMR (400 MHz, CDCl3) δ ppm 11.82 (br. s., 1H), 9.60 (s, 1H), 3.12 (sept, 1H), 1.34 (d, 6H). ES-LCMS: m/z 173.0 (M+1).

Provenance & Evidence