p-Toluenesulfonic acid → 3-(4-fluorophenyl)-6-(4'-hydroxybiphen-4-yl)-3-phenyl-3H-naphtho[2,1-b]pyran

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Reaction Steps

A solution of 4-(4′-hydroxy-4-biphenyl)-2-naphthol (16.14 g, 52 mmol), 1-(4-fluorophenyl)-1-phenylprop-2-yn-1-ol (11.7 g, 52 mmol) and toluene-4-sulphonic acid (0.05 g) in toluene (200 mL) was heated at reflux. After 2 h the mixture was poured into saturated sodium bicarbonate solution (400 mL), extracted with dichloromethane (DCM) (4×100 mL), dried (MgSO4) and the solvent removed under reduced pressure. The residue was chromatographed on silica using EtOAc (10-30% in hexanes) to afford 3-(4-fluorophenyl)-6-(4′-hydroxybiphen-4-yl)-3-phenyl-3H-naphtho[2,1-b]pyran which was collected, the solvent removed under reduced pressure, the residue was filtered through a short plug of silica using DCM as eluent and the solvent removed under reduced pressure to give the title compound (19.37 g, 72%) as an orange solid which was used without further purification.

Provenance & Evidence