Реакция #1519089

Уравнение реакции

sodium hydride

tetraethylene glycol

mesylate

tetraethylene glycol monobenzylether

→

compound 25

Выход 34.5%

Octaethylene glycol monobenzylether

Выход 34.5%

Растворители

tetrahydrofuran

tetrahydrofuran

tetrahydrofuran

Условия реакции

Обработка

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

Методика

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).

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