Ethyl Acetate → Methyl 6-cyano-2,2-diphenyl-1,3-benzodioxole-4-carboxylate

Participants

Reaction Conditions

Reaction Steps

To a solution of methyl 6-bromo-2,2-diphenyl-1,3-benzodioxole-4-carboxylate (800 mg, 1.95 mmol, 1 eq.) in a mixture of 15 mL benzene and 5 mL DMF, Pd(PPh3)4 (225 mg, 0.195 mmol, 0.1 eq.), KCN (127 mg, 1.95 mmol, 1 eq.) and 18-crown-6 (415 mg, 1.56 mmol, 0.8 eq.) was added and the reaction mixture was stirred at 100° C. overnight. Then the reaction mixture was poured into a separatory funnel containing EtOAc and H2O and the aqueous phase was extracted with EtOAc (2×20 mL). The combined organic phases were washed with H2O, then saturated aqueous NaCl solution, dried over MgSO4, and evaporated under reduced pressure. Flash chromatography on silica gel (hexane/EtOAc=20:1→9:1) afforded the desired compound as a colorless solid.

Provenance & Evidence