Hydrochloric Acid → HCID 51198164, compound

Participants

Reaction Steps

To a solution (50 mL) of 1-(5-chloro-2-hydroxyphenyl)ethanone (5.00 g) in tetrahydrofuran were added potassium carbonate (8.10 g), sodium iodide (8.78 g) and 2-chloro-N-methoxy-N-methylacetamide (4.43 g), and the mixture was stirred overnight with heating under reflux. Insoluble material was filtered off, and the filtrate was concentrated under reduced pressure to give a white solid. To a solution (50 mL) of the obtained solid in N,N-dimethylformamide was added 1,8-diazabicyclo[5.4.0]undec-7-ene (4.38 mL), and the mixture was stirred at 120° C. for 2 hr. The reaction mixture was cooled to room temperature, 1N hydrochloric acid was added, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (30% ethyl acetate/hexane) to give the title object compound (2.15 g, 29%) as a brown solid.

Provenance & Evidence