Methyl 1,4-dihydroxy-2-naphthoate → Methyl 2-(4-diethylaminophenyl)-6-hydroxy-2-phenyl-2H-naphtho[1,2-b]pyran-5-carboxylate

Participants

Reaction Steps

Methyl 1,4-dihydroxynaphthalene-2-carboxylate (4.00 g, 18.3 mmol), 1-(4-diethylaminophenyl)-1-phenyl-prop-2-yn-1-ol (4.67 g, 18.3 mmol) and Al2O3 (4.5 g) in toluene (150 mL) was refluxed for 3 hrs, filtered whilst hot and the solvent removed under reduced pressure. The residue was filtered through a short plug of silica using DCM (20% hexane) as eluent followed by a second filtration through silica using DCM as eluent. The residue was crystallised from acetone-MeOH and the product isolated as a yellow solid (4.89 g, 56%)

Provenance & Evidence