Diethyl Ether → 2,6-Diethyl-pyridine

HRID 2387020Notes

Reaction equation

HRID 2387020 reaction equation
[CH2:1]([Mg]Br)[CH3:2].Cl[C:6]1[CH:11]=[CH:10][CH:9]=[C:8](Cl)[N:7]=1.[NH4+].[Cl-].[CH2:15](OCC)[CH3:16]>Cl[Ni]1(Cl)[P](C2C=CC=CC=2)(C2C=CC=CC=2)CCC[P]1(C1C=CC=CC=1)C1C=CC=CC=1>[CH2:15]([C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([CH2:1][CH3:2])[N:7]=1)[CH3:16]

Participants

6

Reactant 4

HCID 3283Diethyl Ether2×HCID 169892,6-DichloropyridineHCID 25517Ammonium ChlorideHCID 178418443HCID 178418443, compound

Product 1

HCID 1367452,6-Diethyl-pyridineYield 89%

Reagents, catalysts & solvents 1

HCID 178418745HCID 178418745, compoundCatalyst

Procedure

A solution of ethylmagnesium bromide in ethyl ether [prepared from Mg (16.5 g, 0.68 mol) and ethyl bromide (50 mL, 0.68 mol) in 500 mL of ether] was added dropwise to a mixture of 2,6-dichloropyridine (50 g, 0.34 mol) and NiCl2(dppp) (1.0 g, 2 mol) in anhydrous ethyl ether (500 mL) at 0° C. under N2 atmosphere. After addition, the resulting mixture was stirred at ambient temperature overnight, was then heated to reflux for about 3 hours. The suspension was poured into crushed ice (200 g) and the mixture was saturated with NH4Cl. The organic layer was separated and the aqueous phase was extracted with ether (200 mL×3). The combined organic layers were washed with water, brine, dried over Na2SO4 and concentrated to give the product (41.1 g, 89%).

Workup

  1. additionAfter addition
  2. temperaturewas then heated
  3. temperatureto reflux for about 3 hours
  4. additionThe suspension was poured
  5. customThe organic layer was separated
  6. extractionthe aqueous phase was extracted with ether (200 mL×3)
  7. washThe combined organic layers were washed with water, brine
  8. dry with materialdried over Na2SO4
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-04dd6941d3b24bb3b603483fab5da690
Source dataset
uspto-grants-2012_09
Patent number
US08268835B2

Reaction notes

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