Tetraethylene Glycol → 1-Phenyl-2,5,8,11,14,17,20,23-octaoxapentacosan-25-ol

To a solution of tetrahydrofuran (140 mL) containing sodium hydride (0.43 g, 18 mmol) was added dropwise a solution of non-polydispersed tetraethylene glycol (3.5 g, 18 mmol) in tetrahydrofuran (10 mL) and the reaction mixture was stirred for 1 h. Then mesylate of non-polydispersed tetraethylene glycol monobenzylether 40 (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 non-polydispersed title compound as a clear oil (2.62 g, 34% yield).

1. additionwas added dropwise
2. stirringthe reaction mixture was stirred overnight
3. customThe crude reaction mixture
4. filtrationwas filtered through Celite (washed, CH2Cl2, 250 mL)
5. washthe filtrate was washed H2O, dried MgSO4
6. customevaporated to dryness
7. customThe resultant oil was chromatographed (silica, ethyl acetate/methanol, 10:1)
8. customchromatographed (silica, chloroform/methanol, 25:1)

ORD record

ord-746ede52140b4ff6b3a407b25a39a3df

Source dataset

uspto-grants-2006_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07084121B2