Sodium hydride → N-[4-(E-2-Cyano-2-pyrid-3-ylethenyl)-2-(2-methylphenyl)benzoyl]methionine, Methyl Ester

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Reaction Steps

To a solution of diethyl 3-pyridylcyanomethyl phosphonate (269 mg) in DME (3 mL) was added NaH (39 mg@60%). To the red solution was added N-[4-formyl-2-(2-methylphenyl)benzoyl] methionine methyl ester (example 10756, 340 mg). After 30 min, the reaction was warmed to reflux for 2.5 h. The reaction was cooled, quenched with water (5 mL), and extracted into EtOAc (20 mL). The organic extracts were washed with brine (5 mL), dried (MgSO4), filtered and concentrated. The residue was purified by silica gel chromatography eluting with 50%-100% EtOAc/hexane to afford two products as colorless oils. The more mobile isomer (68 mg, 13%) was assigned the Z configuration based on a ROESY experiment. MS (APCI(+)) m/e 486 (M+H)+. MS (APCI(−)) m/e 485 M−. The less mobile isomer (246 mg, 48%) was assigned the E configuration based on a ROESY experiment. MS (APCI(+)) m/e 486 (M+H)+. MS (APCI(−)) m/e 485 M−.

Provenance & Evidence