Dicyclohexylcarbodiimide → 8,9-dimethoxy-6-[4'-(4,4,5,5,6,6,7,7,7-nonafluoroheptanoyloxy)biphen-4-yl]-3-phenyl-3-(4-pyrrolidinophenyl)-3H-naphtho[1,2-b]pyran

Participants

Reaction Steps

A solution of 8,9-dimethoxy-6-[4′-hydroxyoxybiphen-4-yl]-3-phenyl-3-(4-pyrrolidinophenyl)-3H-naphtho[1,2-b]pyran (0.95 g, 1.5 mmol) and 4,4,5,5,6,6,7,7,7-nonafluoroheptanoic acid (0.53 g, 1.8 mmol) in DCM (20 mL) containing 4-dimethylaminopyridine (0.02 g) and N,N′-dicyclohexylcarbodiimide (0.33 g, 1.6 mmol) under N2 was stirred at room temperature for 1 h. The resulting mixture was filtered through a short plug of silica using EtOAc (5% in DCM) as eluent. The solvent was removed under reduced pressure and the residue chromatographed on silica using EtOAc (0-25% gradient in toluene) as eluent. The solvent was removed under reduced pressure and the residue washed with toluene/hexanes to give the title compound (0.69 g, 51%) as a pale violet powder, mp 218-219° C. The liquors provided a further 0.16 g (12%) after evaporation and washing with acetone.

Provenance & Evidence