3-Hydroxyacetophenone → HCID 21193540, compound

Participants

Reaction Conditions

Reaction Steps

2.87 g of 3-ethanoylphenol (21 mmol) in anhydrous DMF (30 ml) is cooled to 5° C. (ice bath) under an argon atmosphere, and 0.37 g of sodium hydride (60% suspension in mineral oil; 9.25 mmol) are then added. The mixture is stirred at 5° C. for 10 minutes and then at 20° C. for 2 hours. 0.70 g of 2-(t-butyldimethylsilyl)-5-(4-chlorobutyl)-1-(dimethylsulphamoyl)imidazole (1.85 mmol) (synthesized as described by R. C. Vollinga, W. M. P. B. Menge and H. Timmerman, Rec., Trav., Chem. Pays-Bas, 1993, 112, 123-125) and 45 mg of tetrabutylammonium iodide are added and the mixture is heated at 80° C. under argon for 3 days, then cooled to 20° C. and diluted with diethyl ether until the solution becomes cloudy. The resulting solid is filtered off and the filtrate evaporated to dryness in vacuo, giving a dark orange oil. The latter is subjected to column chromatography (SiO2; using an ethyl acetate/methanol mixture in the ratio 9:1) to give 1-(N,N-dimethyl-sulphamoyl)-5-[4(3-ethanoylphenoxy)butyl]imidazole in the form of a yellow oil.

Provenance & Evidence