Cesium carbonate → Ethyl 4-[(4-{[3-methyl-6-(methyloxy)-2-phenyl-1-naphthalenyl]oxy}phenyl)oxy]butanoate

Participants

Reaction Steps

A round-bottomed flask was charged with 4-{[3-methyl-6-(methyloxy)-2-phenyl-1-naphthalenyl]oxy}phenol (233) (0.300 g, 0.842 mmol), Cs2CO3 (0.824 g, 2.53 mmol), DMF (4 mL), and ethyl 4-bromobutanoate (0.602 mL, 4.21 mmol) under N2. The reaction mixture was refluxed for 15 h and cooled at room temperature. Reaction mixture was partitioned between water and EtOAC (1:1, 100 mL) and the layers were separated. The aqueous phase was further extracted with EtOAc (2×30 mL). The combined organic layer was washed with brine (1×25 mL), dried (Na2SO4), and then concentrated under reduced pressure to afford the crude product. The product was purified by SiO2 column chromatography using hexanes:EtOAc (19:1 to 9:1) as an eluent to give 0.356 g (90%) of the title compound (288) as a colorless oil. LCMS (ESI) m/z 493.27 (M+Na)+.

Provenance & Evidence