Potassium Iodide → HCID 15052463, compound

HRID 327609Notes

Reaction equation

HRID 327609 reaction equation
[CH:1]1([O:6][C:7]2[CH:8]=[C:9]([CH2:15][CH2:16][CH2:17]OS(C3C=CC(C)=CC=3)(=O)=O)[CH:10]=[CH:11][C:12]=2[O:13][CH3:14])[CH2:5][CH2:4][CH2:3][CH2:2]1.[N-:29]=[N+:30]=[N-:31].[Na+].[I-].[K+]>CN(C)C=O>[CH:1]1([O:6][C:7]2[CH:8]=[C:9]([CH2:15][CH2:16][CH2:17][N:29]=[N+:30]=[N-:31])[CH:10]=[CH:11][C:12]=2[O:13][CH3:14])[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 4875Potassium IodideHCID 33557Sodium AzideHCID 15052462HCID 15052462, compound

Product 1

HCID 15052463HCID 15052463, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 0.21 g (0.5 mmol) of 3-(3-cyclopentoxy-4-methoxyphenyl)-1-O-p-toluenesulfonyl-1-propanol in 10 mL of dry N,N-dimethylformamide under a nitrogen atmosphere was added 0.7 g (1.0 mmol) of sodium azide and 0.6 g (0.4 mmol) of potassium iodide in single portions. The mixture was stirred at room temperature for 16 hours at the end of which time the reaction was quenched with excess water and extracted with three, 25 mL portions of chloroform. The combined organic fractions were dried over magnesium sulfate and concentrated under high vacuum to dryness. The resulting oil was purified to an analytically pure oil using liquid chromatography over 50 g of silica gel and eluting with 10% ethyl acetate in hexane followed by drying in vacuo.

Workup

  1. customwas quenched with excess water
  2. extractionextracted with three, 25 mL portions of chloroform
  3. dry with materialThe combined organic fractions were dried over magnesium sulfate
  4. concentrationconcentrated under high vacuum to dryness
  5. customThe resulting oil was purified to an analytically pure oil
  6. washeluting with 10% ethyl acetate in hexane
  7. customby drying in vacuo

Sources & evidence

ORD record
ord-06b35a33a9054606aec63005bcfdf437
Source dataset
uspto-grants-1993_12
Patent number
US05274002

Reaction notes

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