반응 #1519089

반응 방정식

sodium hydride

tetraethylene glycol

mesylate

tetraethylene glycol monobenzylether

→

compound 25

수율 34.5%

Octaethylene glycol monobenzylether

수율 34.5%

용매

tetrahydrofuran

tetrahydrofuran

tetrahydrofuran

반응 조건

후처리

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

실험 절차

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).

출처