Sodium hydride → methyl (E)-3-(4-cyanophenyl)prop-2-enoate

Participants

Reaction Steps

To a stirring suspension of NaH (6.1 g of 60% oil suspension, 153 mmol) and p-cyanobenzaldehyde (20 g, 153 mmol) in tetrahydrofuran (250 mL) at 0° C. was added via addition funnel a solution of trimethyl phosphonoacetate (28 g, 153 mmol) in tetrahydrofuran (50 mL). After stirring for 48 hours, the solvent was removed in vacuo and the crude residue was dissolved in ethyl acetate (500 mL). The ethyl acetate solution was washed once with water, three times with saturated aqueous NaHSO3 and once with brine. The organic phase was then dried with MgSO4, filtered and concentrated in vacuo to give 28 g (98%) of a white solid.

Provenance & Evidence