Sodium Acetate → 2-Chloro-1-(2-hydroxy-4-methoxymethoxybutyl)-4-nitroimidazole

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Reaction Steps

Sodium acetate (3.51 g, 42.82 mmol) and 2-(2-methoxymethoxyethyl)oxirane (10.3 g, 77.86 mmol) were added to 2-chloro-4-nitro-1H-imidazole (5.74 g, 38.93 mmol) in ethanol (60 ml), and the resulting mixture was stirred under reflux for 13.5 hours. The reaction mixture was concentrated under reduced pressure. Water was added to the residue, and the resulting mixture was extracted with methylene chloride. The extract was dried over magnesium sulfate and then concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (methylene chloride/methanol=100/1) and then crystallized from methylene chloride-diisopropyl ether to afford 2-chloro-1-(2-hydroxy-4-methoxymethoxybutyl)-4-nitroimidazole (8.51 g, yield 78%) as a light yellow powder.

Provenance & Evidence