Ethylene Glycol → 3-(1,3-dioxolan-2-yl)pyridine

HRID 1186407Notes

Reaction equation

HRID 1186407 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH:7]=[O:8])[CH:2]=1.[CH2:9](O)[CH2:10][OH:11].O>C1(C)C=CC=CC=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>[O:8]1[CH2:9][CH2:10][O:11][CH:7]1[C:3]1[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=1

Participants

6

Reactant 3

HCID 174Ethylene GlycolHCID 962WaterHCID 103713-Pyridinecarboxaldehyde

Product 1

HCID 2956613-(1,3-dioxolan-2-yl)pyridineYield 89%

Reagents, catalysts & solvents 2

HCID 6101p-Toluenesulfonic acidCatalystHCID 1140TolueneSolvent

Procedure

3-Pyridinecarboxaldehyde (3.00 mL, 31.8 mmol), ethylene glycol (2.66 mL, 47.7 mmol) and p-toluenesulfonic acid (302 mg, 1.59 mmol) were suspended in toluene (100 mL). The mixture was heated to reflux under a nitrogen atmosphere for 2 hours, during which produced water was removed by use of a Dean-Stark trap. Then, a saturated aqueous potassium carbonate solution was added to the reaction mixture, and extraction with ethyl acetate was performed, followed by washing with brine and drying over anhydrous sodium sulfate. The solvent was evaporated off under reduced pressure, and the residue was purified by column chromatography (hexane/ethyl acetate=1/1) to give 3-(1,3-dioxolan-2-yl)pyridine (4.27 g, yield: 89%).

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux under a nitrogen atmosphere for 2 hours, during which
  3. customwas removed by use of a Dean-Stark trap
  4. additionThen, a saturated aqueous potassium carbonate solution was added to the reaction mixture, and extraction with ethyl acetate
  5. washby washing with brine
  6. dry with materialdrying over anhydrous sodium sulfate
  7. customThe solvent was evaporated off under reduced pressure
  8. customthe residue was purified by column chromatography (hexane/ethyl acetate=1/1)

Sources & evidence

ORD record
ord-47d4c96997f24f36b1ad0576339abc7f
Source dataset
uspto-grants-2014_03
Patent number
US08673908B2

Reaction notes

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