18-Crown-6 → 13-Azidotridecanoic acid

HRID 1742446Notes

Reaction equation

HRID 1742446 reaction equation
I[CH:2]([CH3:16])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]([OH:15])=[O:14].[N-:17]=[N+:18]=[N-:19].[Na+].C1OCCOCCOCCOCCOCCOC1>CN(C)C=O>[N:17]([CH2:16][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]([OH:15])=[O:14])=[N+:18]=[N-:19]

Participants

5

Reactant 3

HCID 2855718-Crown-6HCID 33557Sodium AzideHCID 20085175HCID 20085175, compound

Product 1

HCID 45409313-Azidotridecanoic acidYield 66,751.602%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 6 (0.15 g, 0.44 mmol) sodium azide (0.09 g, 1.4 mmol) and 18-crown-6 (0.015 g, 0.057 mmol) in dimethylformamide (3 ml) was stirred at room temperature for 16 h. DMF was distilled under vacuum, cold 2N HCl (2 ml) was added and the mixture was extracted with ethylacetate (10 ml). The organic phase was washed with water (2×10 ml), dried (Na2SO4) and concentrated under reduced pressure to give a pale yellow solid which was purified by flash chromatography (silica gel) using 20% ethylacetate in hexane to afford the title compound 7 (0,075 g, 67%) as a white solid. 1H NMR (CDCl3) δ: 3.26 (t, 2H, J=6.9 Hz); 2.35 (t, 2H, J=7.5 Hz); 1.62 (m, 4H); 1.35 (m, 14H), FABMS: (m/z), 256 (M+H); 230 and 210. HRMS C13H25N3O2Li calc.: 262.2107, found: 262.2164 (M+Li).

Workup

  1. distillationDMF was distilled under vacuum, cold 2N HCl (2 ml)
  2. additionwas added
  3. extractionthe mixture was extracted with ethylacetate (10 ml)
  4. washThe organic phase was washed with water (2×10 ml)
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated under reduced pressure
  7. customto give a pale yellow solid which
  8. customwas purified by flash chromatography (silica gel)

Sources & evidence

ORD record
ord-b99bd9eebf314d3badefe063452f96d2
Source dataset
uspto-grants-1994_08
Patent number
US05338858

Reaction notes

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