Triphenylphosphine → 6-(2-morpholinoethoxy)-2-bromo-3-phenyl-1H-inden-1-one

Participants

Reaction Conditions

Reaction Steps

A flask was charged with 2-bromo-6-hydroxy-3-phenyl-1H-inden-1-one (3.0 g, 10.0 mmol) obtained in Step 5, PPh3 (3.93 g, 1.5 eq), 4-(2-hydroxyethyl)morpholine (1.8 mL, 1.5 eq), and THF (33 mL, 0.3M). The resulting mixture was cooled to 0° C. and diisopropyl azodicarboxylate (DIAD, 2.9 mL, 1.5 eq) was added. The reaction mixture was stirred at 0° C. for 30 min and allowed to increase to ambient temperature. After being stirred for 2 h, the solution was concentrated by rotary evaporation under reduced pressure. The residue was dissolved in EtOAc, washed with H2O and brine, dried over MgSO4, and concentrated in vacuo. The crude product was purified by silica gel column chromatography (EtOAc/hexanes=4:1) to afford the desired product (3.2 g, 78%).

Provenance & Evidence