1-Undecyn-3-ol → 3-[6-(3-Hydroxy-1-undecynyl)-2-pyridinyl]-oxiranebutanol

Participants

Reaction Conditions

Reaction Steps

3-Hydroxy-undec-1-yne (33 mg, 0.194 mmole) and 5,6-epoxy-6[6-bromopyridine-2yl]hexane-1-ol (44 mg, 0.162 mmole) are combined in 1 ml degassed triethylamine in a 25 ml one-neck round bottom flask under argon. The solution is treated with (bis)triphenylphosphine palladium dichloride (3 mg, 0.004 mmole), warmed to 55° C., and is treated with cuprous iodide (1 mg, 0.005 mmole). The reaction mixture is stirred 1.5 hours at 55° C., cooled to room temperature, and the volatiles are removed in vacuo. The residue is partitioned between 1×10 ml diethyl ether and 1×10 ml saturated sodium chloride/ammonium chloride (1:1). The aqueous layer is further extracted with 3×10 ml diethyl ether. The combined organics are dried over magnesium sulfate and concentrated in vacuo to a pale oil.

Provenance & Evidence