Water → HCID 21928374, compound

HRID 1243622Notes

Reaction equation

HRID 1243622 reaction equation
[F:1][C:2]([F:12])([F:11])[C:3]([F:10])([F:9])[CH:4]([OH:8])[CH2:5][CH2:6]I.[N-:13]=[N+:14]=[N-:15].[Na+].O>CS(C)=O>[N:13]([CH2:6][CH2:5][CH:4]([OH:8])[C:3]([F:10])([F:9])[C:2]([F:12])([F:11])[F:1])=[N+:14]=[N-:15]

Participants

5

Reactant 3

HCID 962WaterHCID 33557Sodium AzideHCID 21928329HCID 21928329, compound

Product 1

HCID 21928374HCID 21928374, compoundYield 103.7%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
50 °C

Procedure

A solution of 1,1,1,2,2-pentafluoro-5-iodo-3-pentanol (1.99 g, 7.48 mmol) in dimethylsulfoxide (20 ml) was treated with sodium azide (585 mg, 8.98 mmol) and the reaction was heated to 50° C. After stirring overnight, the reaction was cooled to room temperature. It was then added to water (30 ml) and extracted with diethyl ether (3×30 ml). The combined organics were washed with brine (40 ml) and dried over anhydrous sodium sulphate. Removal of the solvents yielded an orange liquid. Purification by silica gel chromatography using 1:1 hexanes/ethyl acetate gave the title compound as an orange liquid (1.7 g, 100%).

Workup

  1. temperaturethe reaction was cooled to room temperature
  2. extractionextracted with diethyl ether (3×30 ml)
  3. washThe combined organics were washed with brine (40 ml)
  4. dry with materialdried over anhydrous sodium sulphate
  5. customRemoval of the solvents
  6. customyielded an orange liquid
  7. customPurification by silica gel chromatography

Sources & evidence

ORD record
ord-4a76f00418ac46ada95dd79dfeb073b3
Source dataset
uspto-grants-2006_10
Patent number
US07119109B2

Reaction notes

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