Reacción #1519089

Ecuación de reacción

sodium hydride

tetraethylene glycol

mesylate

tetraethylene glycol monobenzylether

→

compound 25

Rendimiento 34.5%

Octaethylene glycol monobenzylether

Rendimiento 34.5%

Disolventes

tetrahydrofuran

tetrahydrofuran

tetrahydrofuran

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.ADDITIONwas added dropwise
2. 2
   workup.STIRRINGthe reaction mixture was stirred overnight
3. 3
   OtroThe crude reaction mixture
4. 4
   Filtraciónwas filtered through Celite (washed, CH2Cl2, 250 mL)
5. 5
   Lavadothe filtrate was washed H2O, dried MgSO4
6. 6
   Otroevaporated to dryness
7. 7
   OtroThe resultant oil was chromatographed (silica, ethyl acetate/methanol, 10:1)
8. 8
   Otrochromatographed (silica, chloroform/methanol, 25:1)

Procedimiento

To a solution of tetrahydrofuran (140 mL) containing sodium hydride (0.43 g, 18 mmol) was added dropwise a solution of monodispersed tetraethylene glycol (3.5 g, 18 mmol) in tetrahydrofuran (10 mL) and the reaction mixture was stirred for 1 h. Then mesylate of monodispersed tetraethylene glycol monobenzylether 24 (6.0 g, 16.5 mmol) dissolved in tetrahydrofuran (10 mL) was added dropwise and the reaction mixture was stirred overnight. The crude reaction mixture was filtered through Celite (washed, CH2Cl2, 250 mL) and the filtrate was washed H2O, dried MgSO4, and evaporated to dryness. The resultant oil was chromatographed (silica, ethyl acetate/methanol, 10:1) and chromatographed (silica, chloroform/methanol, 25:1) to afford the monodispersed compound 25 as a clear oil (2.62 g, 34% yield).

Fuente