Trimethylsilylacetylene → Methyl 4-cyclobutyl-2-methyl-5-((trimethylsilyl)ethynyl)benzoate

Participants

Reaction Conditions

Reaction Steps

A mixture of methyl 4-cyclobutyl-5-iodo-2-methylbenzoate (compound 152.3, 1.32 g, 4 mmol), trimethylsilylacetylene (663 μl, 4.8 mmol), Pd(PPh3)2Cl2 (85 mg, 0.12 mmol) and copper iodide (CuI, 46 mg, 0.24 mmol) in THF (8 ml) and triethylamine (2 ml) was degassed and then heated to 80° C. for 1.5 hours under nitrogen. After cooling to ambient temperature, the reaction was filtered through celite and concentrated. The residue was dissolved in ethyl acetate (EtOAc), washed with brine, dried over MgSO4 and concentrated. The residue was purified by flash chromatography (SiO2; 3% EtOAc in Hexane) to give 1.17 g (97%) of the title compound as a liquid. 1H NMR (400 MHz, CDCl3) δ 8.01 (s, 1H), 7.15 (s, 1H), 4.01-3.75 (m, 4H), 2.63 (s, 3H), 2.54-2.31 (m, 2H), 2.27-2.12 (m, 2H), 2.12-1.98 (m, 1H), 1.94-1.80 (m, 1H), 0.28 (s, 9H).

Provenance & Evidence