Pentane → 2-[(4-methoxyphenyl)methoxy]-3-[(4-methoxyphenyl)methoxylpropyl]-1H-imidazole

Participants

Reaction Steps

A solution of 1-[2-hydroxy-3-[(4-metoxyphenyl)methoxy]propyl]-1H-imidazole (206 g, 0.79M) in dry tetrahydrofuran (3700 ml) was added dropwise to a stirred slurry of sodium hydride (38 g of a 60% dispersion in oil, 0.95M; prewashed with pentane) in dry tetrahydrofuran (200 ml) at below 5° C. and under a gentle stream of dry nitrogen. The resulting mixture was stirred at room temperature for 1 hour and 4-methoxybenzyl chloride (123.2 g, 0.79M) in dry tetrahydrofuran (100 ml) was added. The resulting mixture was stirred at room temperature, protected from light, for 3 days.

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