Water → HCID 57392868, compound

Participants

Reaction Steps

To a solution of cyanomethylphosphonic acid diethyl ester (8.1 mL, 51.6 mmol) in anhydrous THF (50 mL) was added lithium bis(trimethylsilyl)amide (1.0 M solution in THF, 51.6 mL, 51.6 mmol) at 0° C. and stirred for 30 min at room temperature followed by addition of (3-ethoxy-4-methoxy-phenyl)-(3-hydroxy-4-methoxy-phenyl)-methanone (5.20 g, 17.2 mmol) in THF (40 mL) and refluxed overnight. The reaction mixture was poured into water (50 mL), extracted with CH2Cl2 (2×60 mL). The combined organic phases were washed with brine (60 mL), dried over MgSO4, and purified via flash column chromatography (EtOAc/Hexane) to give E/Z-3-(3-ethoxy-4-methoxy-phenyl) -3-(3-hydroxy-4-methoxy-phenyl)-acrylonitrile as an off-white solid (5.26 g, 94% yield). The product was used in the next step without further purification.

Provenance & Evidence