反应 #1519089

反应方程式

sodium hydride

tetraethylene glycol

mesylate

tetraethylene glycol monobenzylether

→

compound 25

收率 34.5%

Octaethylene glycol monobenzylether

收率 34.5%

溶剂

tetrahydrofuran

tetrahydrofuran

tetrahydrofuran

反应条件

后处理

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

实验过程

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).

来源