Sodium Azide → 4-Azido-1,1,1-trifluoro-2-butanol

HRID 1243615Notes

Reaction equation

HRID 1243615 reaction equation
[F:1][C:2]([F:19])([F:18])[CH:3]([OH:17])[CH2:4][CH2:5]OS(C1C=CC(C)=CC=1)(=O)=O.[N-:20]=[N+:21]=[N-:22].[Na+]>CS(C)=O.O>[N:20]([CH2:5][CH2:4][CH:3]([OH:17])[C:2]([F:19])([F:18])[F:1])=[N+:21]=[N-:22]

Participants

5

Reactant 2

HCID 33557Sodium AzideHCID 101086924-Toluenesulfonic acid 4,4,4-trifluoro-3-hydroxybutyl ester

Product 1

HCID 219283544-Azido-1,1,1-trifluoro-2-butanolYield 100%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

A solution of 4-toluenesulfonic acid 4,4,4-trifluoro-3-hydroxybutyl ester (1.30 g, 4.36 mmol) in DMSO (7 mL) was treated with sodium azide (0.306 g, 4.71 mmol) at is ambient temperature and then heated at 50° C. for 23 h. The mixture was diluted with cold water and extracted with diethyl ether. The combined organic extracts were washed (brine), dried, and evaporated without heat to give the product as a yellow oil (0.737 g, 100%).

Workup

  1. customat is ambient temperature
  2. extractionextracted with diethyl ether
  3. washThe combined organic extracts were washed (brine)
  4. customdried
  5. customevaporated
  6. temperaturewithout heat

Sources & evidence

ORD record
ord-01cd3ad5857c426ebf238cc5017250eb
Source dataset
uspto-grants-2006_10
Patent number
US07119109B2

Reaction notes

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