Reacción #1361229

Ecuación de reacción

4-[(2-trimethylsiloxyethyl)ethylamino]iodobenzene

trimethylsilylacetylene

→

yellow oil

Rendimiento 92.0%

4-[(2-Trimethylsiloxyethyl)-ethylamino]tri-methylsilylethynylbenzene

Rendimiento 92.0%

Disolventes

triethylamine

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.ADDITIONA mixture containing 10.9 g, that
2. 2
   Otrodegassed under nitrogen for 15 minutes
3. 3
   workup.ADDITIONwas added with vigorous
4. 4
   OtroThe cooled reaction mixture
5. 5
   Filtraciónwas filtered
6. 6
   workup.ADDITIONdiluted with ethyl ether
7. 7
   Extracciónextracted with dilute HCL
8. 8
   OtroThe organic phase was separated
9. 9
   Secadodried over anhydrous sodium sulfate
10. 10
    Otrothe solvent was removed under reduced pressure
11. 11
    Otrochromatographed on silica gel with 4% ethyl acetate-hexane

Procedimiento

A mixture containing 10.9 g, that is 30 mmole, 4-[(2-trimethylsiloxyethyl)ethylamino]iodobenzene from the previous step, 1.0 g, that is 1.4 mmole bis(triphenylphosphine)palladium(II) chloride from Aldrich Chemical Co., and 74 mg, that is 0.75 mmole cuprous chloride, from Aldrich Chemical Co. in 50 m triethylamine was stirred and degassed under nitrogen for 15 minutes. Next 3.5 g, that is, 36 mmole trimethylsilylacetylene from Aldrich chemical Co. was added with vigorous mechanical stirring at room temperature and the final mixture was stirred at 80° C. for 1 hour. The cooled reaction mixture was filtered, diluted with ethyl ether and extracted with dilute HCL. The organic phase was separated, dried over anhydrous sodium sulfate, and the solvent was removed under reduced pressure. The dark residue was flash column chromatographed on silica gel with 4% ethyl acetate-hexane to give 9.2 g of yellow oil at a 92% yield.

Fuente