Potassium Hydroxide → 4-(4-Benzyl-morpholin-2-yl)-phenol

Participants

Reaction Steps

To a suspension of 4-benzyl-6-(4-bromo-phenyl)-morpholine (8.70 g; 26.19 mmol) in water (25 mL) and 1,4-dioxane (25 mL) was added KOH (3.23 g; 57.61 mmol), tris(dibenzylideneaceton)dipalladium(0) (479.6 mg; 0.52 mmol) and di-tert-butyl-(2′,4′,6′-triisopropyl-biphenyl-2-yl)-phosphane (444.8 mg; 1.05 mmol). The resulting mixture was heated under reflux for two hours. After cooling to RT the reaction mixture was concentrated in vacuo. The residue was partitioned between EtOAc and 5% aqueous NaHCO3 solution. The organic layer was dried (Na2SO4), filtered and concentrated in vacuo. The residue was purified by column chromatography (SiO2, Et2O:hexanes 1:1) to afford 4-(4-benzyl-morpholin-2-yl)-phenol (3.67 g).

Provenance & Evidence