(2-(Dimethylamino)ethyl)triphenylphosphonium bromide → (E)-3-[4-(3-Dimethylaminopropenyl)phenyl]acrylic Acid

Participants

Reaction Steps

(E)-3-[4-(3-Dimethylaminopropenyl)phenyl]acrylic acid, methyl ester was prepared by the following way: (2-dimethylaminoethyl)triphenylphosphonium bromide (7.2 g, 17.4 mmol) in 30 mL of DMF was treated with KHMDS (27 mL, 1.01 equiv., 0.5 M in toluene) at −78° C. for one hour. At −40° C., 3-(4-formylphenyl)acrylic acid, methyl ester (2.54 g, 13.3 mmol, prepared according to the procedure of Syper, L.; Miochowski, J. Synthesis, 1984, 9, 747-752) was added dropwise. The resulting mixture was stirred for 12 hours at rt and quenched with water. Extraction with EtOAc, drying over MgSO4 and evaporation in vacuo gave a residue that was purified via flash chromatography with DCM:MeOH (90:10) as eluting solvent. The title compound (1.1 g, 34%) was obtained as an orange oil.

Provenance & Evidence