Triethyl phosphonoacetate → HCID 86758305, compound

Participants

Reaction Steps

9 ml of ethyl diethylphosphonoacetate was added dropwise to a suspension of 60% sodium hydride in oil (1.93 g) in 40 ml tetrahydrofuran and stirred at room temperature for 30 minutes. A solution of 4′-(methoxymethoxy)acetophenone (6.70 g) in 40 ml tetrahydrofuran was added dropwise to the reaction mixture, followed by stirring at room temperature for 17 hours and subsequently at reflux for 4 days. The solvent was evaporated, and the reaction mixture was mixed with water and then extracted with ethyl acetate. The resulting organic layer was washed with water and brine, and then dried over magnesium sulfate. The drying agent was filtered off and the solvent was evaporated to give a residue, which was then purified via column chromatography on silica gel (hexane:ethyl acetate=10:1) to provide ethyl (E)-3-[4-(methoxymethoxy)phenyl]-2-butenoate (3.91 g, 42%) as a colorless oil and ethyl (Z)-3-[4-(methoxymethoxy)phenyl]-2-butenoate (425 mg, 4.6%) as a colorless oil, respectively.

Provenance & Evidence