Potassium Carbonate → 2-n-Butyl-1-pivalyloxymethylimidazole-5-aldehyde

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Reaction Steps

A suspension of 2-butylimidazol-5-aldehyde (16,92 g, 0.111 mol, prepared by manganese dioxide oxidation of the alcohol, prepared in Example 1, Method 2), chloromethyl pivalate (21.77 g, 0.145 mol), and potassium carbonate (20.07 g, 0.145 mol) in 200 ml of dimethylformamide was stirred at ambient temperature under argon for four days. The solids were removed by filtration and washed with ether. The combined filtrates were partitioned between diethyl ether and water. The ether phase was washed successively with water and brine, dried over magnesium sulfate and concentrated under vacuum to give 23.6 g of 2-n-butyl-1-pivalyloxymethylimidazole-5-aldehyde.

Provenance & Evidence