Sodium Iodide → N-methoxy-N,3,5-trimethyl-1-benzofuran-2-carboxamide

Participants

Reaction Conditions

Reaction Steps

To a solution (50 mL) of 1-(2-hydroxy-5-methylphenyl)ethanone (5.00 g) in N,N-dimethylformamide were added potassium carbonate (9.20 g), sodium iodide (9.98 g) and 2-chloro-N-methoxy-N-methylacetamide (5.04 g), and the mixture was stirred at 50° C. for 5 hr then at 80° C. overnight. The insoluble material was filtered off, 1,8-diazabicyclo[5.4.0]undec-7-ene (5.00 mL) was added to the filtrate and the mixture was stirred at 120° C. for 2 hr. 1N Hydrochloric acid was added to quench the reaction, 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 (20% ethyl acetate/hexane) to give the title object compound (3.78 g, 49%) as a brown oil.

Provenance & Evidence