Trimethylsilylacetylene → Methyl 2-(2-((trimethylsilyl)ethynyl)phenyl)acetate

Participants

Reaction Steps

A mixture of methyl 2-(2-iodophenyl)acetate (I1) (4.65 g, 16.8 mmol), PdCl2(PPh3)2 (295 mg, 421 μmol), CuI (80.0 mg, 421 μmol) and (trimethylsilyl)acetylene (2.80 mL, 20.2 mmol) in dry degassed THF (20 mL) and Et3N (20 mL) was stirred at room temperature for 16 hours. The volatiles were removed under reduced pressure to give a black residue which was adsorbed onto silica gel and purified using column chromatography (0-5% EtOAc in petroleum benzine 40-60° C.) to give the title compound I2 as a light brown liquid (4.63 g, 99%); 1H NMR (400 MHz, CDCl3) δ 7.48 (dd, J=7.5, 0.8 Hz, 1H), 7.32-7.14 (m, 3H), 3.84 (s, 2H), 3.71 (s, 3H), 0.26 (s, 9H). LCMS-B: rt 6.64 min.

Provenance & Evidence