Imidazole → HCID 21288112, compound

Participants

Reaction Steps

9.82 g (35.4 mmol) of 2-acetyl-6-(1-bromoethyl)naphthalene, 6.38 g (70.9 mmol) of sodium imidazolide (from 3.1 g (70.9 mmol) of sodium hydride dispersion (55%) and 4.83 g (70.9 mmol) of imidazole) and 0.588 g (3.54 mmol) of potassium iodide in 100 ml of absolute N,N-dimethylformamide are stirred at 100° C. (24 hours). The mixture is then evaporated in vacuo, the residue is taken up in 4N HCl, the solution is extracted with ethyl acetate, and the aqueous phase is neutralized with sodium carbonate solution. It is then extracted 4× with dichloromethane, and the dichloromethane phase is dried and evaporated in vacuo. The residue is filtered through silica gel using ethyl acetate/methanol 8:1. 6.48 g (70%) of 2-acetyl-6-[1-(1-imidazolyl)ethyl]naphthalene are obtained as an oil. RF (ethyl acetate/methanol 8:1): 0.15.

Provenance & Evidence