Phenylacetylene → HCID 54568033, compound

Participants

Reaction Steps

A solution of t-butyl { 5-acetyl-2[(trifluoromethyl)sulfonyloxy]-phenoxy}acetate(1.0 g, 1.3 mmol) and phenylacetylene (0.33 mL, 3.0 mmol) in 20 mL triethylamine in a thick walled pyrex tube is degassed with nitrogen for 15 minutes. Bis(triphenylphosphine)-palladium(II) chloride (35 mg, 0.05 mmol) and copper (I) iodide (10 mg, 0.05 mmol) are added, and the vessel is sealed, and heated to 60° for 18 hours. After cooling, the triethylamine is removed in vacuo, and the residue is dissolved in ether (100 mL) and washed with 1 N HCl (1×100 mL) and brine (1×50 mL), dried over MgSO4, and concentrated in vacuo. Chromatography (silica, 5:1 hexane/EtOAc) yields t-butyl [5-acetyl-2-(2-phenylethynyl)-phenoxy]-acetate, along with 10% starting material. This mixture is carried on to the next step.

Provenance & Evidence