Carbon tetrabromide → 2,3-Dioleyloxypropyl azide

HRID 376412

Reaktionsgleichung

Reaktionsgleichung von HRID 376412
[CH2:1]([O:19][CH2:20][CH:21]([CH2:41]O)[O:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30]/[CH:31]=[CH:32]\[CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH3:40])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8]/[CH:9]=[CH:10]\[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].[N-:43]=[N+:44]=[N-:45].[Li+].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Br)(Br)(Br)Br>CN(C)C=O>[CH2:23]([O:22][CH:21]([CH2:20][O:19][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8]/[CH:9]=[CH:10]\[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])[CH2:41][N:43]=[N+:44]=[N-:45])[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30]/[CH:31]=[CH:32]\[CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH3:40]

Komponenten

6

Edukt 4

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 88163Lithium azideHCID 53803432,3-Bis[(9Z)-9-octadecen-1-yloxy]-1-propanol

Produkt 1

HCID 867518532,3-Dioleyloxypropyl azideAusbeute 100 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a mixture of 1.00 g (1.7 mmol) of 1,2-O-dioleylglycerol, 0.83 g (17 mmol) of lithium azide, 0.89 g (3.4 mmol) of triphenylphosphine, and 1.13 g (3.4 mmol) of carbon tetrabromide was added 10 ml of N,N-dimethylformamide in bolus and the mixture was stirred at ambient temperature for 3 hours. After completion of the reaction, the solvent was distilled off and the residue was diluted with water and extracted with ether. The ether layer was washed with water, dried, and concentrated, and the residue was purified by column chromatography (silica gel/n-hexane-ethyl acetate) to provide 1.03 g (100%) of 2,3-dioleyloxypropyl azide as oil.

Aufarbeitung

  1. customAfter completion of the reaction
  2. distillationthe solvent was distilled off
  3. additionthe residue was diluted with water
  4. extractionextracted with ether
  5. washThe ether layer was washed with water
  6. customdried
  7. concentrationconcentrated
  8. customthe residue was purified by column chromatography (silica gel/n-hexane-ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-5da49e96076848b5af3f147b2d5e7ef0
Quelldatensatz
uspto-grants-2000_02
Patentnummer
US06020317

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