Imidazole → HCID 22324681, compound

Participants

Reaction Steps

A mixture of sodium hydride (60% dispersion in oil, 32 mg, 0.81 mmol), acetonitrile (0.4 mL), and imidazole (275 mg, 4.0 mmol) was stirred at room temperature for 10 min, whereupon a solution of 2-methyl-2-{[5-oxo-1-(2-phenylethyl)-5,6,7,8-tetrahydro-2-naphthalenyl]oxy}propyl trifluoromethane-sulfonate (190 mg, 0.40 mmol) in acetonitrile (0.8 mL) was added. The resulting mixture was stirred at reflux for 20 min and was then concentrated. The residue was purified by dry-flash column chromatography (SiO2, 1-10% 2-propanol-dichloromethane) to give 6-[2-(1H-imidazol-1-yl)-1,1-dimethylethoxy]-5-(2-phenylethyl)-3,4-dihydro-1(2H)-naphthalenone as a colorless oil, 126 mg, 92% yield. NMR spectrum was consistent with structure. MS EI: M+• 388.2149 (M+• 388.2151).

Provenance & Evidence