Isopropyl iodide → Methyl 1-(propan-2-yl)-1H-imidazole-4-carboxylate

Participants

Reaction Steps

Add sodium hydride (2.87 g, 71.7 mmol, 60% in mineral oil) portion-wise over 10 minutes to a cooled (0° C.) solution of 1H-imidazole-4-carboxylic acid methyl ester (6.03 g, 47.8 mmol) in dimethylformamide (150 ml). Remove the cooling bath and stir at room temperature for 4.5 hrs. Cool the mixture to 0° C. and add isopropyl iodide (8.94 g, 52.6 mmol) dropwise over 10 min. Remove the cooling bath and stir at room temperature for 20 hrs. Quench the mixture with saturated aqueous ammonium chloride and extract with ethyl acetate (3×). Wash the combined extracts with brine, dry over sodium sulfate, filter and concentrate under reduced pressure to give an oil. Purify the oil by flash chromatography (silica gel) eluting with 25% acetone/hexanes to provide the product as an oil (1.41 g, 8.4 mmol, 17% yield). M/S (m/z): 169 (M+H).

Provenance & Evidence