Hydrochloric Acid → 3-(4-fluorophenyl)-6-(4'-(hexanoyloxy)biphen-4-yl)-3-phenyl-3H-naphtho[2,1-b]pyran

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Reaction Steps

Hexanoyl chloride (5.01 g, 37 mmol) was added dropwise to a solution of 3-(4-fluorophenyl)-6-(4′-hydroxybiphen-4-yl)-3-phenyl-3H-naphtho[2,1-b]pyran (19.37 g, 37 mmol) in DCM (100 mL) containing pyridine (20 mL) at 0° C. After ½ h additional hexanoyl chloride (5.01 g, 37 mmol) was added. Stirring was continued for a further ½ h more, the solution was poured into HCl (2 M, 400 mL), separated and extracted with DCM (2×100 mL), the combined organic phases were washed with water saturated sodium bicarbonate (200 mL), dried (MgSO4) and the solvent removed under reduced pressure. The residue was filtered through a short plug of silica using DCM (50% in hexanes) as eluent. The solvent was removed under reduced and the residue triturated alternately with hexanes and methanol twice. The residue was dried under vacuum to give the title compound (16.51 g, 72%) as a yellow foam, mp 64-65° C.

Provenance & Evidence