Lithium hydroxide, monohydrate → 2-Bromo-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazole-4-carboxylic acid

Participants

Reaction Steps

To a stirred solution of methyl 2-bromo-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazole-4-carboxylate (2.85 g, 8.50 mmol) in mixed solvents (THF/MeOH/water; 2:2:1; 50 mL) was added LiOH H2O (1.07 g, 25.5 mmol) at 0° C. The cold bath was removed and stirring was continued for 2 h. The reaction mixture was concentrated in vacuo, diluted with water and washed with MTBE. The aqueous layer was neutralized with 1.5N HCl and extracted with EtOAc (2×). The combined organic layers were dried over Na2SO4 and concentrated in vacuo to provide the title compound (2.4 g, 88%) as a white solid. 1H NMR (CDCl3) δ 12.54 (br s, 1H), 8.14 (s, 1H), 5.33 (s, 2H), 3.54 (t, J=8.0 Hz, 2H), 0.85 (t, J=8.0 Hz, 2H), 0.01 (s, 9H); MS(ESI+) m/z 323.0 (M+H)+.

Provenance & Evidence