1-Acetylnaphthalene → HCID 10552746, compound

Participants

Reaction Steps

A mixture of 4-iodo-1-tritylimidazole (commercially available) (4.5 g, 10.3 mmol) in dichloromethane (50 mL) at 22° C. was treated with ethyl magnesium bromide (3.48 mL, 10.4 mmol, 3M in ether) and allowed to react for 1 h. Anhydrous CeCl3 (3.3 g, 13.4 mmol) was added and the mixture was stirred for 30 m. A solution of 1-acetonaphthone (commercially available from Aldrich) (2.6 g, 15.9 mmol) in dichloromethane was added via syringe at 22° C. and stirred for 16 h. The mixture was quenched with a sat. solution of ammonium chloride (50 mL). The residue was isolated in a typical aqueous workup and purified by chromatography on silica gel with 50% EtOAc:hexane to give 1-naphthalen-1-yl-1-(1-trityl-1H-imidazol-4-yl)-ethanol (Intermediate H1) as a solid, 2.44 g (49%).

Provenance & Evidence