Réaction #1519089

Équation de réaction

sodium hydride

tetraethylene glycol

mesylate

tetraethylene glycol monobenzylether

→

compound 25

Rendement 34.5%

Octaethylene glycol monobenzylether

Rendement 34.5%

Solvants

tetrahydrofuran

tetrahydrofuran

tetrahydrofuran

Conditions de réaction

Traitement

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

Mode opératoire

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).

Source