Isopropyl iodide → HCID 58356347, compound

Participants

Reaction Steps

1,1-Dimethylethyl 3-formyl-1H-pyrazole-5-carboxylate (600 mg) and cesium carbonate (996 mg) were dissolved in acetonitrile (60 ml). 2-Iodopropane (0.305 ml) was added and the mixture was stirred at RT for 20 h. A further portion of 2-iodopropane (0.03 ml) was added and the mixture was stirred at RT for 16 h. The solvent was removed in vacuo. The reaction mixture was diluted with water (80 ml) and DCM (80 ml) and separated using a hydrophobic frit. The aqueous layer was extracted with a further quantity of DCM (2×50 ml) using a hydrophobic frit. The solvent was removed in vacuo and the residue was purified by flash chromatography on silica gel (50 g silica), eluting with a gradient of 0-100% ethyl acetate in cyclohexane to give the title compound (377 mg), and a mixture (213 mg) of both isomers. The mixture was purified by flash chromatography on silica gel (20 g silica), eluting with a gradient of 0-50% ethyl acetate in cyclohexane to give another quantity (114 mg) of the title compound (114 mg) as a colourless oil.

Provenance & Evidence