Reaktion #1361229

Reaktionsgleichung

4-[(2-trimethylsiloxyethyl)ethylamino]iodobenzene

trimethylsilylacetylene

→

yellow oil

Ausbeute 92.0%

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

Ausbeute 92.0%

Lösungsmittel

triethylamine

Reaktionsbedingungen

Aufarbeitung

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

Vorschrift

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.

Quelle