2-Ethylpyridine → HCID 14762641, compound

HRID 1622051Notes

Reaction equation

HRID 1622051 reaction equation
[CH2:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][N:4]=1)[CH3:2].C([Li])CCC.F[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=1>O1CCCC1>[CH:1]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=1)([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][N:4]=1)[CH3:2]

Participants

5

Reactant 3

HCID 75232-EthylpyridineHCID 97462-FluoropyridineHCID 178418339Butyllithium

Product 1

HCID 14762641HCID 14762641, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-80 °C

Procedure

58.0 g (540 mmol) of 2-ethylpyridin were dissolved in 550 ml tetrahydrofurane and cooled to −80° C. 200 ml (540 mmol) of butyl lithium (2.7 M in heptane) were added over a period of thirty minutes. After stirring at −20° C. for two hours 26.3 g (270 mmol) of 2-fluoropyridine were added. The mixture was stirred under reflux for thirty minutes, then cooled and poured on 500 ml ice. The layers were separated and the aqueous layer was extracted with 200 ml dichloromethane. The combined organic layers were dried with sodium sulphate and concentrated under reduced pressure. The oily residue was distilled under reduced pressure to yield 39.8 g (80%) of yellow oil that was used in the next synthesis without further purification.

Workup

  1. additionwere added
  2. temperatureunder reflux for thirty minutes
  3. temperaturecooled
  4. customThe layers were separated
  5. extractionthe aqueous layer was extracted with 200 ml dichloromethane
  6. dry with materialThe combined organic layers were dried with sodium sulphate
  7. concentrationconcentrated under reduced pressure
  8. distillationThe oily residue was distilled under reduced pressure

Sources & evidence

ORD record
ord-260bfdfec0d34f3ba720cc9f42f266a0
Source dataset
uspto-grants-2014_07
Patent number
US08778512B2

Reaction notes

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