Water → HCID 86616658, compound

Participants

Reaction Conditions

Reaction Steps

7-Fluoro-6-(methyloxy)-2-phenyl-3-propyl-1-naphthalenol (137) (0.42 g, 1.34 mmol) was dissolved in DMF (5 mL). To this solution was added 4-fluorobenzaldehyde (0.34 g, 2.68 mmol) followed by Cs2CO3 (0.57 g, 1.74 mmol). The mixture was heated at 100° C. for 36 h, poured into water (50 mL) and extracted with EtOAc (2×75 mL). The combined organic extract was washed with water, brine, dried over Na2SO4, filtered, and the filtrate was concentrated to give the crude product as reddish brown oil. The crude product was purified by flash chromatography over SiO2 eluted with a gradient from hexanes to 15% EtOAc in hexanes to give 0.38 g (69%) of the title compound (138) as a yellow viscous oil. 1H NMR (400 MHz, CDCl3): δ 0.81 (t, J=7.4 Hz, 3H), 1.40-1.60 (m, 2H), 2.53 (t, J=7.8 Hz, 2H), 4.02 (s, 3H), 6.66 (d, J=8.8 Hz, 2H), 7.06-7.12 (m, 2H), 7.18-7.25 (m, 4H), 7.40 (d, J=12.1 Hz, 1H), 7.56-7.64 (m, 3H), 9.80 (s, 1H). LCMS (ESI): m/z 415 (M+H)+.

Provenance & Evidence