Trimethylsilylacetylene → Methyl 4-methyl-3-((trimethylsilyl)ethynyl)benzoate

Participants

Reaction Conditions

Reaction Steps

A mixture of methyl 3-iodo-4-methylbenzoate (2.0 g, 7 mmol), trimethylsilylacetylene (1.2 ml, 8 mmol), Pd(PPh3)4 (0.42 g, 0.3 mmol), CuI (0.137 g, 0.7 mmol) and diisopropylethylamine (2.5 ml, 11.4 mmol) in THF (20 ml) was heated at 50° C. for 12 hrs under nitrogen atmosphere. The reaction mixture was cooled to ambient temperature and filtered through a Celite® bed. The clear filtrate was concentrated and the residue purified by flash chromatography on silica gel (elution with 2% ethyl acetate in n-hexane) to provide methyl 4-methyl-3-[(trimethylsilyl)ethynyl]benzoate.

Provenance & Evidence