3-Butyn-1-OL → methyl 4-(4-hydroxy-1-butynyl)phenylacetate

Participants

Reaction Steps

To a solution of methyl 4-bromophenylacetate (229 mg, 1.0 mmole) and 3-butyn-1-ol (151 μL, 2.0 mmole) in triethylamine (4.0 mL) was added cuprous bromide (18 mg, 0.12 mmole) and tetra(triphenylphosphine)palladium (46 mg, 0.04 mmole), and the mixture refluxed under a nitrogen atmosphere for 1 hr 20 min. The mixture was evaporated in vacuo and the residue partitioned with water and ether. The organic phase was washed with brine, dried over magnesium sulfate and concentrated in vacuo to an oil. Flash chromatography on silica gel in 7:3 hexane:ethyl acetate afforded the title compound (175 mg) as an oil NMR (CDCl3): δ 1.69 (s, 1H); 2.71 (t, 2H); 3.63 (s, 2H); 3.71 (s, 3H); 3.83 (t, 2H); 7.22 (d, 2H); 7.38 (d, 2H).

Provenance & Evidence