Sodium Azide → Azido-PEG2-Phosphonic Ester

HRID 2204957Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2204957
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 vaccuo. The crude material was purified by flash chromatography on a COMBIFLASH® system (ISCO) 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 vaccuo
  7. customThe crude material was purified by flash chromatography on a COMBIFLASH® system (ISCO)

Quellen und Nachweise

ORD-Eintrag
ord-84c114cf562244bdbb6b1d221d08cf2c
Quelldatensatz
uspto-grants-2016_06
Patentnummer
US09365506B2

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