Methanesulfonic Acid → HCID 68487123, compound

Participants

Reaction Steps

A solution of 4-chloro-2-cyclopropyl-5-{[(phenylmethyl)oxy]methyl}-1H-imidazole (1.02 g, 3.9 mmol) and methanesulfonic acid (9.7 mL, 149 mmol) in chloroform (22 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) and then with 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-cyclopropyl-1H-imidazol-5-yl)methanol as a brown solid. A solution of this solid and manganese dioxide (2.1 g, 24.8 mmol) in CH2Cl2 (12 mL) and 1,4-dioxane (6 mL) was heated under reflux for 6 h. The reaction mixture was cooled to RT, filtered through Celite and washed thoroughly with CH2Cl2. The filtrate was concentrated and dried to provide the title compound (0.282 g, 41%) as a brown solid. 1H NMR (400 MHz, CDCl3) δ ppm 11.05 (br. s., 1H), 9.49 (s, 1H), 1.95-2.04 (m, 1H), 1.09-1.17 (m, 2 H), 1.03-1.09 (m, 2H). ES-LCMS: m/z 171.0 (M+1).

Provenance & Evidence