Ethylene Glycol → HCID 58416469, compound

HRID 1014994Notes

Reaction equation

HRID 1014994 reaction equation
[Cl:1][C:2]1[C:7]([C:8](=[O:10])[CH3:9])=[CH:6][CH:5]=[CH:4][N:3]=1.[CH2:11](O)[CH2:12][OH:13].O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[Cl:1][C:2]1[C:7]([C:8]2([CH3:9])[O:13][CH2:12][CH2:11][O:10]2)=[CH:6][CH:5]=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 174Ethylene GlycolHCID 521998p-Toluenesulfonic acid monohydrateHCID 109426973-Acetyl-2-chloropyridine

Product 1

HCID 58416469HCID 58416469, compoundYield 77.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

1-(2-Chloro-pyridin-3-yl)-ethanone (2.21 g, 14.2 mmol, 1.0 equiv), ethylene glycol (4.41 g, 71.0 mmol, 5.0 equiv) and p-toluenesulfonic acid monohydrate (1.35 g, 7.1 mmol, 0.5 equiv) are dissolved in toluene (100 mL). The resulting mixture is heated overnight under Dean Stark conditions. After cooling to room temperature the mixture is washed twice with saturated NaHCO3 solution, brine, dried over Na2SO4 and evaporated in vacuo. The residue is purified by flash column chromatography (10% to 50% ethyl acetate in heptane) to yield 2.19 g of the title compound.

Workup

  1. temperatureThe resulting mixture is heated overnight under Dean Stark conditions
  2. washis washed twice with saturated NaHCO3 solution, brine
  3. dry with materialdried over Na2SO4
  4. customevaporated in vacuo
  5. customThe residue is purified by flash column chromatography (10% to 50% ethyl acetate in heptane)

Sources & evidence

ORD record
ord-3ffd4df8486e48e28ee35c7636a194a9
Source dataset
uspto-grants-2011_07
Patent number
US07985753B2

Reaction notes

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