Reaktion #1361228

Reaktionsgleichung

Ethyl ether

4-[(2-hydroxyethyl)ethylamino]iodobenzene

triethylamine

chlorotrimethylsilane

→

clear viscous oil

Ausbeute 92.0%

4-[(2-Trimethylsiloxyethyl)-ethylamino]iodobenzene

Ausbeute 92.0%

Lösungsmittel

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONwas added slowly
2. 2
   Temperaturwhile maintaining the reaction temperature below 10° C
3. 3
   Extraktionextracted with brine
4. 4
   SonstigeThe organic layer was separated
5. 5
   Trocknendried over anhydrous sodium sulfate
6. 6
   SonstigeAfter removing the solvent under reduced pressure
7. 7
   Sonstigechromatographed on silica gel with 2% ethyl acetate-hexane

Vorschrift

A solution of 14.5 g, that is 50 mmole of 4-[(2-hydroxyethyl)ethylamino]iodobenzene and 6.0 g, that is 60 mmole triethylamine, from Aldrich Chemical Co. in 90 ml tetrahydrofuran ("THF") was stirred in an ice-water bath under nitrogen. Next, 5.5 g, 51 mmole chlorotrimethylsilane, from Aldrich Chemical Co. was added slowly while maintaining the reaction temperature below 10° C. The mixture was stirred for 30 minutes then warmed to room temperature for 1 hour. Ethyl ether was added and extracted with brine. The organic layer was separated and dried over anhydrous sodium sulfate. After removing the solvent under reduced pressure, the residue was flash column chromatographed on silica gel with 2% ethyl acetate-hexane to give 16.63 g of a clear viscous oil at a 92% yield.

Quelle