Trifluoroacetic acid → HCID 66778197, compound

Participants

Reaction Steps

To a mixture of 1-(3-methyl-1-benzofuran-2-yl)-2-phenoxyethanone (697 mg) synthesized above, methyl 4-aminobenzoate (399 mg), triethylamine (2.93 mL) and methylene chloride (10 mL) was added titanium (IV) chloride (344 μL) at 0° C. under argon atmosphere, and the mixture was stirred overnight at room temperature. Saturated aqueous sodium hydrogen carbonate solution was added to quench the reaction, methylene chloride was evaporated in an evaporator, and the residue was extracted with ethyl acetate. The extract was washed with saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure to give a dark brown oil. To a solution (20 mL) of the obtained oil in tetrahydrofuran were added acetic acid (2 mL) and sodium cyanoborohydride (329 mg), and the mixture was stirred at room temperature for 15 min. Trifluoroacetic acid (2 mL) was added to the reaction mixture, and the mixture was further stirred at room temperature for 3 hr. Saturated aqueous sodium hydrogen carbonate solution was added to quench the reaction, and the reaction 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 (25% ethyl acetate/hexane) to give the title object compound (279 mg, 27%) as a yellow solid.

Provenance & Evidence