Sodium Azide → 17-Azido-3,6,9,12,15-pentaoxaheptadecan-1-ol

HRID 1695326Notes

Reaction equation

HRID 1695326 reaction equation
S([O:11][CH2:12][CH2:13][O:14][CH2:15][CH2:16][O:17][CH2:18][CH2:19][O:20][CH2:21][CH2:22][O:23][CH2:24][CH2:25][O:26][CH2:27][CH2:28]O)(C1C=CC(C)=CC=1)(=O)=O.[N-:30]=[N+:31]=[N-:32].[Na+]>CN(C)C=O>[N:30]([CH2:28][CH2:27][O:26][CH2:25][CH2:24][O:23][CH2:22][CH2:21][O:20][CH2:19][CH2:18][O:17][CH2:16][CH2:15][O:14][CH2:13][CH2:12][OH:11])=[N+:31]=[N-:32]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 104331623,6,9,12,15-Pentaoxaheptadecane-1,17-diol, 1-4-methylbenzenesulfonate

Product 1

HCID 5757086617-Azido-3,6,9,12,15-pentaoxaheptadecan-1-ol

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-[2-(2-{2-[2-(2-tosyloxy-ethoxy)-ethoxy]-ethoxy}-ethoxy)-ethoxy]-ethanol (Loiseau, F. A.; Hii, K. K.; Hill, A. M. J. Org. Chem. 2004, 69, 639) (4.5 g) in dimethylformamide (30 mL), was added sodium azide (0.89 g). The solution was stirred at 70° C. for 18h and solvent was then removed in vacuo to a residue. Dichloromethane was added and the resulting precipitate was filtered off. The organic layer was concentrated in vacuo to give 2-[2-(2-{2-[2-(2-Azido-ethoxy)-ethoxy]-ethoxy}-ethoxy)-ethoxy]-ethanol (3.1 g):

Workup

  1. customwas then removed in vacuo to a residue
  2. additionDichloromethane was added
  3. filtrationthe resulting precipitate was filtered off
  4. concentrationThe organic layer was concentrated in vacuo

Sources & evidence

ORD record
ord-e2424a0b3cd6448eb48e43aafd78ec74
Source dataset
uspto-grants-2012_04
Patent number
US08163736B2

Reaction notes

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