Acetic Acid → 7-({4-[(4-chlorophenyl)ethynyl]benzyl}amino)-2,2-dimethyl-1H-1,3-benzodioxin-4-one

Participants

Reaction Conditions

Reaction Steps

A mixture of 7-[((E)-{4-[(4-chlorophenyl)ethynyl]phenyl}methylidene)amino]-2,2-dimethyl-4H-1,3-benzodioxin-4-one (1.65 g, 3.97 mmol), sodium triacetoxyborohydride (2.52 g, 11.9 mmol) and acetic acid (0.34 mL, 5.95 mmol) in anhydrous DCE (100 mL) was heated at 50° C. for 3 h. Then the reaction mixture was diluted with H2O (100 mL) and a saturated aqueous solution of NaHCO3 (100 mL) and extracted with DCM (3×200 mL). The combined organic layers were dried over MgSO4 and the solvents were removed under reduced pressure. Precipitation by addition of pentane and filtration gave 1.30 g of the titled compound as a pale yellow powder (77%). M− (ESI): 415.9. HPLC, Rt: 5.05 min (Purity: 98.0%).

Provenance & Evidence