Triethyl phosphonoacetate → ethyl (2E)-3-cyclopropylacrylate

Participants

Reaction Conditions

Reaction Steps

To a stirred suspension of NaH (60% in oil, 2.1 g, 51.5 mmol) in dry THF (50 mL) was added dropwise ethyl(diethoxyphosphoryl)acetate (10.6 g, 47.1 mmol) at 0° C. under N2 atmosphere. The resulting mixture was stirred at 0° C. for 0.5 hr and added dropwise a solution of cyclopropanecarbaldehyde (3.0 g, 42.9 mmol) in dry THF (50 mL). After the addition, the mixture was stirred at rt for 16 hrs. Then the reaction mixture was quenched by addition of 5% NH4Cl (100 mL) at 0° C. and extracted with EtOAc (100 mL). The organic layer was washed with brine (100 mL), dried over Na2SO4 and concentrated in vacuo. The residue was purified by column chromatography (silica gel, petroleum ether: EtOAc=30:1) to give the title compound (5.3 g, 88.3% yield) as a colorless oil.

Provenance & Evidence