1-Pentyne → Methyl 2-(pent-1-ynyl)benzoate

Participants

Reaction Steps

Pent-1-yne (5.6 mL, 57.2 mmol) was added to methyl 2-iodobenzoate (5.6 mL, 38.2 mmol), copper(I) iodide (1.0 g, 5.72 mmol) and Pd(PPh3)4 (1.3 g, 1.14 mmol) in DMF (5 mL) and Et3N (1 mL) at RT for 3 hrs. The reaction was partitioned between Et2O and 0.1 M HClaqueous. The resulting organic phase was washed with 0.1 M HClaqueous, NaHCO3aqueous and brine. Organic phase was then anhydrified over Na2SO4 and dried under reduced pressure to give methyl 2-(pent-1-ynyl)benzoate (7.8 g) as a dark oil. The crude will be used in the next step without further purification.

Provenance & Evidence