Sodium Azide → 3-(1-Azidotridecyl)-5-trimethylsilylfuran

HRID 1090893Notes

Reaction equation

HRID 1090893 reaction equation
Cl[CH:2]([C:15]1[CH:19]=[C:18]([Si:20]([CH3:23])([CH3:22])[CH3:21])[O:17][CH:16]=1)[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14].[N-:24]=[N+:25]=[N-:26].[Na+]>CN(C)C=O>[N:24]([CH:2]([C:15]1[CH:19]=[C:18]([Si:20]([CH3:23])([CH3:22])[CH3:21])[O:17][CH:16]=1)[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14])=[N+:25]=[N-:26]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 150370763-(1-Chlorotridecyl)-5-trimethylsilylfuran

Product 1

HCID 190198473-(1-Azidotridecyl)-5-trimethylsilylfuran

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 3-(1-chlorotridecyl)-5-trimethylsilylfuran (468 mg, 1.31 mmol) and sodium azide (852 mg, 13.1 mmol) in dry dimethylformamide (2 ml) was stirred at 60 degrees for 6 days. Most of the solvent was evaporated under high vacuum and the residue dissolved in water. Extraction (ethyl ether) and evaporation of the dried (magnesium sulfate) extracts gave an oil, which was flash chromatographed on silica using 5% ethyl ether/hexane. Fractions with Rf of about 0.73 on evaporation gave the title azide as a very pale yellow oil.

Workup

  1. customMost of the solvent was evaporated under high vacuum
  2. dissolutionthe residue dissolved in water
  3. extractionExtraction (ethyl ether) and evaporation of the
  4. dry with materialdried (magnesium sulfate)
  5. customextracts gave an oil, which
  6. customchromatographed on silica using 5% ethyl ether/hexane
  7. customFractions with Rf of about 0.73 on evaporation

Sources & evidence

ORD record
ord-d2d1d575b37e437787ecd91257fedb66
Source dataset
uspto-grants-1992_01
Patent number
US05082954

Reaction notes

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