Lithium Hydroxide → HCID 66777647, compound

Participants

Reaction Conditions

Reaction Steps

To a mixture of methyl 4-{[(3-bromo-5-methoxy-1-benzofuran-2-yl)(cyclohexyl)methyl]amino}benzoate (1.46 g) synthesized above, zinc cyanide (362 mg) and N,N-dimethylformamide (30 mL) was added tetrakis(triphenylphosphine)palladium (0) (357 mg), and after deaeration, the mixture was stirred under argon atmosphere at 80° C. overnight. Water was added to the reaction mixture, 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 (40% ethyl acetate/hexane) to give a yellow solid. To a solution (10 mL) of the obtained solid in tetrahydrofuran was added 1N lithium hydroxide aqueous solution (2.88 mL), and the mixture was stirred overnight with heating under reflux. Ethanol (10 mL) and water (10 mL) were added to the reaction mixture, and the mixture was stirred with heating under reflux for 3 hr. 1N lithium hydroxide aqueous solution (1.44 mL) was additionally added, and the mixture was stirred overnight with heating under reflux, and concentrated under reduced pressure. The residue was dissolved in water (20 mL), and 1N hydrochloric acid (4.35 mL) was added at 0° C. The resulting precipitate was collected by filtration to give the title object compound (547 mg, 94%) as a pale-yellow solid.

Provenance & Evidence