Reacción #1361228

Ecuación de reacción

Ethyl ether

4-[(2-hydroxyethyl)ethylamino]iodobenzene

triethylamine

chlorotrimethylsilane

→

clear viscous oil

Rendimiento 92.0%

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

Rendimiento 92.0%

Disolventes

tetrahydrofuran

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.ADDITIONwas added slowly
2. 2
   Temperaturawhile maintaining the reaction temperature below 10° C
3. 3
   Extracciónextracted with brine
4. 4
   OtroThe organic layer was separated
5. 5
   Secadodried over anhydrous sodium sulfate
6. 6
   OtroAfter removing the solvent under reduced pressure
7. 7
   Otrochromatographed on silica gel with 2% ethyl acetate-hexane

Procedimiento

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.

Fuente