Water → 3-Methoxy-1-(5-phenyl-2-thienyl)naphthalene

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Reaction Steps

A mixture of 3-methoxynaphthalene-1-yl trifluoromethanesulfonate (2.7 g, 8.82 mmol), 5-phenyl-2-thiopheneboronic acid (2.7 g, 13.24 mmol), sodium carbonate (1.4 g, 13.24 mmol) was mixed in de-gassed toluene (50 ml) and ethanol (50 ml), under nitrogen. Pd(PPh3)4 (153 mg, 1 mol %) was added and the mixture heated to reflux for 18 h. The solution was allowed to cool, poured into water (200 ml), extracted with dichloromethane (2×100 ml), dried (Na2SO4), and the solvent removed under reduced pressure. The resulting residue was dissolved in DCM and filtered through a short plug of silica. The solvent was removed under reduced pressure to give a red/brown solid, which was flash chromatographed on silica using EtOAc-hexane (1:9). The fractions were combined and the solvent removed to give the title compound (1.87 g, 67%) as a green solid.

Provenance & Evidence