Water → Methyl 5-[(4-ethylphenyl)methyl]-3-hydroxy-2-naphthoate

Participants

Reaction Conditions

Reaction Steps

Under a nitrogen stream, the known compound methyl 3-hydroxy-5-trifluoromethanesulfonyloxy-2-naphthoate (Bull. Korean Chem. Soc. 2000, 21, 757; 82.3 mg, 0.23 mmol), diphenylphosphino ferrocene palladium dichloride (17.3 mg, 0.021 mmol), 2-[(4-ethylphenyl)methyl]-4,4,5,5-tetramethyl-[1,3,2]dioxaborane (57.8 mg, 0.24 mmol) and cesium carbonate (228.6 mg, 0.70 mmol) were dissolved in tetrahydrofuran (2.0 mL). Water (0.2 mL) was added thereto, and then the mixture was stirred for 30 minutes at 100° C. in a microwave apparatus. Water was added thereto, and the resultant mixture was extracted with ethyl acetate. The organic layer was washed with 1 N hydrochloric acid and saturated brine, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The resulting residue was purified by silica gel flash column chromatography (developing solution=ethyl acetate:n-hexane (1:20)), to thereby obtain the titled compound (55.8 mg, 74%).

Provenance & Evidence