Potassium Carbonate → (S)-3-Oxiranyl-pyridine

HRID 1351917Notes

Reaction equation

HRID 1351917 reaction equation
Cl[CH2:2][C@@H:3]([C:5]1[CH:6]=[N:7][CH:8]=[CH:9][CH:10]=1)[OH:4].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[N:7]1[CH:8]=[CH:9][CH:10]=[C:5]([C@@H:3]2[CH2:2][O:4]2)[CH:6]=1

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 11400917(1R)-2-Chloro-1-(pyridin-3-yl)ethan-1-ol

Product 1

HCID 13319559(S)-3-Oxiranyl-pyridineYield 94.9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of (R)-2-chloro-1-pyridin-3-ylethanol (2.0 g, 12.7 mmol) in acetonitrile (100 ml) is added potassium carbonate (7.02 g). The mixture is refluxed for 2.5 hours, and cooled to room temperature. The mixture is filtered, and the filtrate is distilled off under reduced pressure. The resultant is purified by silica gel column chromatography (methanol/chloroform=1/100) to give the title compound (R)-(pyridin-3-yl)oxirane (1.46 g, yield: 94%) as pale yellow oil.

Workup

  1. temperatureThe mixture is refluxed for 2.5 hours
  2. filtrationThe mixture is filtered
  3. distillationthe filtrate is distilled off under reduced pressure
  4. customThe resultant is purified by silica gel column chromatography (methanol/chloroform=1/100)

Sources & evidence

ORD record
ord-91eb07056e8b49769259744368f67664
Source dataset
uspto-grants-2007_05
Patent number
US07217724B2

Reaction notes

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