Sodium Azide → (R)-4-azido-1,1,1-trifluoro-2-butanol

HRID 1243613Notes

Reaction equation

HRID 1243613 reaction equation
[F:1][C:2]([F:9])([F:8])[C@H:3]([OH:7])[CH2:4][CH2:5]I.[N-:10]=[N+:11]=[N-:12].[Na+]>CS(C)=O.O>[N:10]([CH2:5][CH2:4][C@@H:3]([OH:7])[C:2]([F:9])([F:8])[F:1])=[N+:11]=[N-:12]

Participants

5

Reactant 2

HCID 33557Sodium AzideHCID 22874097(R)-1,1,1-trifluoro-4-iodo-2-butanol

Product 1

HCID 21064884(R)-4-azido-1,1,1-trifluoro-2-butanolYield 100.1%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

A solution of (R)-1,1,1-trifluoro-4-iodo-2-butanol (3.30 g, 13.0 mmol) in DMSO (22 mL) was treated with sodium azide (0.930 g, 14.3 mmol) at ambient temperature, followed by heating at 50° C. for 20 h. The mixture was diluted with cold water (250 mL) and extracted with diethyl ether. The combined organic extracts were washed (brine), dried, and evaporated without heat to give the product as a pale yellow oil (2.20 g, 100%).

Workup

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

Sources & evidence

ORD record
ord-d2c398c1965c4c7d87929722f998f964
Source dataset
uspto-grants-2006_10
Patent number
US07119109B2

Reaction notes

Loading…