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

HRID 24994

Reaktionsgleichung

Reaktionsgleichung von HRID 24994
[H-].[Na+].[CH2:3]([OH:15])[CH2:4][O:5][CH2:6][CH2:7][O:8][CH2:9][CH2:10][O:11][CH2:12][CH2:13]O.S([O-])(=O)(=O)C.[CH2:21]([O:28][CH2:29][CH2:30][O:31][CH2:32][CH2:33][O:34][CH2:35][CH2:36][O:37][CH2:38][CH2:39][OH:40])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>O1CCCC1>[CH2:21]([O:28][CH2:29][CH2:30][O:31][CH2:32][CH2:33][O:34][CH2:35][CH2:36][O:37][CH2:38][CH2:39][O:40][CH2:13][CH2:12][O:11][CH2:10][CH2:9][O:8][CH2:7][CH2:6][O:5][CH2:4][CH2:3][OH:15])[C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1

Komponenten

6

Edukt 4

HCID 8200Tetraethylene GlycolHCID 24758Sodium hydrideHCID 85257MethanesulfonateHCID 110769571-Phenyl-2,5,8,11-tetraoxatridecan-13-ol

Produkt 1

HCID 574377031-Phenyl-2,5,8,11,14,17,20,23-octaoxapentacosan-25-olAusbeute 34,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel3×

Versuchsvorschrift

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).

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-26e75621b35249a29877c32d5ebb71b6
Quelldatensatz
uspto-grants-2005_02
Patentnummer
US06858580B2

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