Carbon tetrabromide → 2,3-Dioleyloxypropyl azide

HRID 724757

Reaction equation

HRID 724757 reaction equation
[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]

Participants

6

Reactant 4

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

Product 1

HCID 867518532,3-Dioleyloxypropyl azideYield 100%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-bfca62dd0eeb4eeb90172f288e21daae
Source dataset
uspto-grants-1998_01
Patent number
US05705188

Linked notes

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