反応 #2307977

反応方程式

sodium hydride

tetraethylene glycol

mesylate

tetraethylene glycol monobenzylether

→

compound 25

収率 34.5%

Octaethylene glycol monobenzylether

収率 34.5%

溶媒

tetrahydrofuran

tetrahydrofuran

tetrahydrofuran

反応条件

後処理

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

実験手順

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).

出典