Water → HCID 10966372, compound

Participants

Reaction Conditions

Reaction Steps

t-BuOK (4.57 g, 40.7 mmol) was added in small portions to a solution of triethyl phosphonoacetate (8.10 mL, 40.7 mmol) and 4-(allyloxy)benzaldehyde (Intermediate D, 6.00 g, 37.0 mmol) in THF (100 mL) cooled at 0° C., leading to the formation of a viscous mixture. After 30 min, water (20 mL) was added and the solvent was removed by rotatory evaporation. The crude residue was dissolved in EtOAc (100 mL) and washed with water (2×100 mL); the organic layer was dried over anhydrous Na2SO4 and filtered. After removal of the solvent, the residue was purified by column chromatography on silica gel (7% EtOAc/Hexanes), affording 7.76 g of (E)-ethyl 3-(4-(allyloxy)phenyl)acrylate [Rf=0.4 (10% EtOAc/Hexanes), colorless oil, 90% yield].

Provenance & Evidence