Reacción #1361230

Ecuación de reacción

4-[(2-trimethylsiloxyethyl)ethylamino]trimethylsilylethynyl-benzene

tetrabutylammonium fluoride

Ethyl ether

→

viscous yellow oil

Rendimiento 88.1%

4-[(2-Hydroxyethyl)ethylamino]-ethynylbenzene

Rendimiento 88.1%

Disolventes

methanol THF

THF

Condiciones de reacción

Tratamiento posterior

1. 1
   Otroprepared in the previous step
2. 2
   workup.ADDITIONwas added dropwise
3. 3
   Extracciónthe mixture was extracted with water
4. 4
   OtroThe organic layer was separated
5. 5
   Secadodried over anhydrous sodium sulfate
6. 6
   Otrothe solvent was removed under reduced pressure
7. 7
   Otrochromatographed on silica gel with 35% ethyl acetate-hexane

Procedimiento

To a solution of 5.0 g, that is 15 mmole of 4-[(2-trimethylsiloxyethyl)ethylamino]trimethylsilylethynyl-benzene, prepared in the previous step, dissolved in 60 mL of methanol-THF (1:1) mixture, 33 ml, that is 33 mmole, of 1M tetrabutylammonium fluoride in THF, from Aldrich Chemical Co. was added dropwise. The solution was stirred at room temperature for 1 hour. Ethyl ether was added and the mixture was extracted with water. The organic layer was separated, dried over anhydrous sodium sulfate and the solvent was removed under reduced pressure. The crude product was flash column chromatographed on silica gel with 35% ethyl acetate-hexane to produce 2.5 g of a viscous yellow oil at an 88% yield.

Fuente