Sodium Azide → 2-Azido-2-(6-(2,2,2-trifluoroethoxy)pyridin-3-yl)ethanol

HRID 623479Notes

Reaction equation

HRID 623479 reaction equation
[N-:1]=[N+:2]=[N-:3].[Na+].Cl([O-])(=O)(=O)=O.[Li+].[O:11]1[CH2:13][CH:12]1[C:14]1[CH:15]=[CH:16][C:17]([O:20][CH2:21][C:22]([F:25])([F:24])[F:23])=[N:18][CH:19]=1>C(#N)C>[N:1]([CH:12]([C:14]1[CH:19]=[N:18][C:17]([O:20][CH2:21][C:22]([F:25])([F:23])[F:24])=[CH:16][CH:15]=1)[CH2:13][OH:11])=[N+:2]=[N-:3]

Participants

5

Reactant 3

HCID 33557Sodium AzideHCID 23665649Lithium perchlorateHCID 874265125-(Oxiran-2-yl)-2-(2,2,2-trifluoroethoxy)pyridine

Product 1

HCID 1317351792-Azido-2-(6-(2,2,2-trifluoroethoxy)pyridin-3-yl)ethanolYield 37%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Sodium azide (1.05 g, 16.2 mmol) and lithium perchlorate (6.45 g, 60.7 mmol) are added to a solution of 5-(oxiran-2-yl)-2-(2,2,2-trifluoroethoxy)pyridine (0.89 g, 4.04 mmol, Step-5, single enantiomer) in acetonitrile (100 mL) is refluxed with stirring for 5 hours. White precipitate is filtrated and filtrate is concentrated in vacuo. The residue is poured into water, extracted with ethyl acetate and dried over sodium sulfate and concentrated in vacuo. The residue is purified by column chromatography on silica gel eluting with n-hexane/ethyl acetate (1:1) to give 0.39 g (37% yield) of the title compound as colorless oil.

Workup

  1. temperatureis refluxed
  2. filtrationWhite precipitate is filtrated
  3. concentrationfiltrate is concentrated in vacuo
  4. additionThe residue is poured into water
  5. extractionextracted with ethyl acetate
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated in vacuo
  8. customThe residue is purified by column chromatography on silica gel eluting with n-hexane/ethyl acetate (1:1)

Sources & evidence

ORD record
ord-659ebd49bbab4b7985d88178920293ae
Source dataset
uspto-grants-2016_04
Patent number
US09302991B2

Reaction notes

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