Triethylamine → 10-(4-Tributylstannyl-[1,2,3]triazol-1-yl)-decanoic acid

Participants

Reaction Steps

10-Azidodecanoic acid (2.0 g, 9.5 mmol) in THF (50 mL) is treated with tributylstannyl acetylene (2.99 g, 9.5 mmol) copper(I)iodide (90 mg 0.47 mmol) and triethylamine (256 mg, 2.54 mmol) at room temperature with constant stirring for 24 h. The reaction is then filtered through celite and concentrated in vacuo to a gum, and then chromatographed on silica in a gradient of 10-40% ethyl acetate in petrol. The main fraction is collected and concentrated in vacuo to give 10-(4-tributylstannyl-[1,2,3]triazol-1-yl)-decanoic acid (3.22 g, 0.8 mmol).

Provenance & Evidence