Sodium Azide → Azido-PEG2-Phosphonic Ester

HRID 629951Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 629951
I[CH2:2][CH2:3][O:4][CH2:5][CH2:6][O:7][CH2:8][CH2:9][P:10](=[O:17])([O:14][CH2:15][CH3:16])[O:11][CH2:12][CH3:13].[N-:18]=[N+:19]=[N-:20].[Na+]>CCO.O>[N:18]([CH2:2][CH2:3][O:4][CH2:5][CH2:6][O:7][CH2:8][CH2:9][P:10](=[O:17])([O:14][CH2:15][CH3:16])[O:11][CH2:12][CH3:13])=[N+:19]=[N-:20]

Komponenten

5

Edukt 2

HCID 33557Sodium AzideHCID 86667775Diethyl 2-(2-(2-iodoethoxy)ethoxy)ethylphosphonate

Produkt 1

HCID 86667776Azido-PEG2-Phosphonic Ester

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 962WaterLösungsmittel2×

Versuchsvorschrift

To a solution of diethyl 2-(2-(2-iodoethoxy)ethoxy)ethylphosphonate (1 eq) in EtOH (0.2 M) was added sodium azide (5 eq) in water (1.4 M). The reaction mixture was heated at reflux overnight. The mixture was then diluted with water, extracted with EtOAc (3 times). The combined organic layers were washed brine, dried over anhydrous Na2SO4, and concentrated en vacuo. The crude material was purified by flash chromatography on a COMBIFLASH™ system using 0-5% MeOH/DCM to give diethyl 2-(2-(2-azidoethoxy)ethoxy)ethylphosphonate as colorless oil.

Aufarbeitung

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux overnight
  3. extractionextracted with EtOAc (3 times)
  4. washThe combined organic layers were washed brine
  5. dry with materialdried over anhydrous Na2SO4
  6. concentrationconcentrated en vacuo
  7. customThe crude material was purified by flash chromatography on a COMBIFLASH™ system

Quellen und Nachweise

ORD-Eintrag
ord-f97def86a20241b9bf7721de819d49b6
Quelldatensatz
uspto-grants-2016_04
Patentnummer
US09315530B2

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