Cesium carbonate → 4-[(6-Methoxy-3-methyl-2-phenyl-1-naphthyl)oxy]benzaldehyde

Participants

Reaction Steps

A round-bottomed flask was charged with 3-methyl-6-(methyloxy)-2-phenyl-1-naphthalenol (7) (2.5 g, 9.5 mmol), 4-fluorobenzaldehyde (1.22 mL, 11.4 mmol), Cs2CO3 (4.04 g, 12.4 mmol), and anhydrous DMF (25 mL) under N2. The reaction mixture was refluxed for 3 h. Reaction mixture was cooled at room temperature and purified by SiO2 column chromatography using hexanes:EtOAc (19:1 to 4:1) as an eluent to afford 3.41 g (98%) of the title compound as a white foam. 1H NMR (400 MHz, CDCl3): δ 9.80 (s, 1H), 7.68 (d, J=9.2 Hz, 1H), 7.62 (d, J=8.4 Hz, 2H), 7.61 (d, J=5.2 Hz, 1H), 7.25 (d, J=7.6 Hz, 2H), 7.22 (d, J=5.2 Hz, 1H), 7.15 (d, J=2.4 Hz, 1H), 7.14 (d, J=1.6 Hz, 1H), 7.11 (s, 1H), 7.07 and 7.04 (dd, J1=9.2 Hz, J2=2.4 Hz, 1H), 6.71 (d, J=8.8 Hz, 2H), 3.94 (s, 3H), 2.26 (s, 3H). LCMS (ESI) m/z, 368.92 (M+H)+.

Provenance & Evidence