Propargyl alcohol → HCID 69990034, compound

Participants

Reaction Conditions

Reaction Steps

Tetrakis(triphenylphosphine)palladium(0) (0.41 g, 0.14 mmol), cuprous iodide (0.5 g, 0.25 mmol), and propargyl alcohol (0.29 mL, 4.91 mmol) were added to a solution of 3-(3-bromophenyl)propionic acid tert-butyl ester (2.13 g, 7.08 mmol) in pyrrolidine (8 mL) under an argon atmosphere at room temperature. The mixture was heated at 75-80° C. for 5 hours. After cooling to room temperature, saturated ammonium chloride was added and the mixture was extracted with diethyl ether. The extract was washed with brine, dried over magnesium sulfate, and concentrated to dryness. Purification by flash chromatography, eluting with hexane/ethyl acetate (85:15), gave 3-[3-(3-hydroxyprop-1-ynyl)phenyl]propionic acid tert-butyl ester as a yellow oil (0.21 g, 33%).

Provenance & Evidence