Diethyl Ether → HCID 86680926, compound

Participants

Reaction Conditions

Reaction Steps

35.0 g (90.4 mmol) of (6-bromonaphthalen-2-yloxy)triisopropylsilane are initially introduced in 120 ml of THF and 70 ml of diisopropylamine, and, after addition of 3.50 g (5.0 mmol) of bis(triphenylphosphine)palladium(II) chloride and 1.0 g (5.3 mmol) of copper(I) iodide, 25.0 g (0.255 mol) of trimethylsilylacetylene in 30 ml of THF are added dropwise at 70° C. The batch is left to stir for 4 h at 70° C. and overnight at room temp., 150 ml of MTB ether are added, and the mixture is washed three times with water, dried over sodium sulfate and evaporated in vacuo. Filtration of the crude product through silica gel with heptane gives 2-triisopropylsilanyloxy-6-trimethylsilanylethynylnaphthalene, which is employed in the next step without further purification.

Provenance & Evidence