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Sodium Azide → 1,2-Di-O-(n-hexadecyl)-3-O-(3-azido-2-hydroxypropyl)-glycerol

HRID 1701599
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1701599
[N-:1]=[N+:2]=[N-:3].[Na+].[CH2:5]([O:21][CH2:22][CH:23]([CH2:41][O:42][CH2:43][CH:44]1[O:46][CH2:45]1)[O:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH3:40])[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20]>O.O1CCOCC1>[CH2:5]([O:21][CH2:22][CH:23]([CH2:41][O:42][CH2:43][CH:44]([OH:46])[CH2:45][N:1]=[N+:2]=[N-:3])[O:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH3:40])[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 2

HCID 33557Sodium Azide2×HCID 234661141,2-Di-O-(n-hexadecyl)-3-O-(2,3-epoxypropyl)-glycerol

Produkt 1

HCID 234660851,2-Di-O-(n-hexadecyl)-3-O-(3-azido-2-hydroxypropyl)-glycerolAusbeute 62 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

A solution of sodium azide (0.5 g., 7.7 mmoles) in water (5 ml.) was added to a refluxing solution of 1,2-di-O-(n-hexadecyl)-3-O-(2,3-epoxypropyl)-glycerol (3.3 g., 5.5 mmoles) in 1,4-dioxane (100 ml.), and the resulting solution stirred at reflux for 16 hours. Since the reaction was not yet complete, additional sodium azide (0.5 g., 7.7 mmoles) was added and the reaction stirred at reflux for another 16 hours. The reaction solution was then cooled, concentrated in vacuo, diluted with water (100 ml.) and extracted with ether (3×100 ml.). The combined ether extract was washed with water (100 ml.), dried (MgSO4), filtered and evaporated in vacuo to an oil which solidified on standing [2.2 g., 62% yield, ir (CHCl3) 2105 cm-1 ].

Aufarbeitung

  1. temperatureat reflux for 16 hours
  2. stirringthe reaction stirred
  3. temperatureat reflux for another 16 hours
  4. temperatureThe reaction solution was then cooled
  5. concentrationconcentrated in vacuo
  6. additiondiluted with water (100 ml.)
  7. extractionextracted with ether (3×100 ml.)
  8. extractionThe combined ether extract
  9. washwas washed with water (100 ml.)
  10. dry with materialdried (MgSO4)
  11. filtrationfiltered
  12. customevaporated in vacuo to an oil which

Quellen und Nachweise

ORD-Eintrag
ord-9a87b9e6fbe44615ae305d29b4474352
Quelldatensatz
uspto-grants-1980_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04193999

Notizen zur Reaktion

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