Ethyl Acetate → 4-(Diethoxymethyl)pyridine

HRID 1186412Notes

Reaction equation

HRID 1186412 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([CH:7]=[O:8])=[CH:3][CH:2]=1.C([O-])([O-])[O:10][CH2:11][CH3:12].C(=O)(O)[O-].[Na+].[C:20](OCC)(=O)[CH3:21]>C(O)C.C1(C)C=CC(S(O)(=O)=O)=CC=1>[CH2:20]([O:8][CH:7]([O:10][CH2:11][CH3:12])[C:4]1[CH:5]=[CH:6][N:1]=[CH:2][CH:3]=1)[CH3:21]

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 133894-PyridinecarboxaldehydeHCID 516892Sodium BicarbonateHCID 53630039Ethylorthoformate

Product 1

HCID 153891924-(Diethoxymethyl)pyridineYield 78%

Reagents, catalysts & solvents 2

HCID 6101p-Toluenesulfonic acidCatalystHCID 702EthanolSolvent

Procedure

4-Pyridinecarboxaldehyde (3.00 mL, 31.4 mmol), ethyl orthoformate (15.7 mL, 94.2 mmol) and p-toluenesulfonic acid (229 mg, 1.57 mmol) were dissolved in ethanol (60.0 mL), and the mixture was heated to reflux under a nitrogen atmosphere for 10 hours. The reaction was stopped by addition of a saturated aqueous sodium bicarbonate solution 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 silica gel column chromatography (hexane/ethyl acetate=1/1) to give 4-(diethoxymethyl)pyridine (4.41 g, yield: 78%).

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux under a nitrogen atmosphere for 10 hours
  3. washby washing with brine
  4. dry with materialdrying over anhydrous sodium sulfate
  5. customThe solvent was evaporated off under reduced pressure
  6. customthe residue was purified by silica gel column chromatography (hexane/ethyl acetate=1/1)

Sources & evidence

ORD record
ord-22eb51c7d69541a6bb2afa84e7de2b07
Source dataset
uspto-grants-2014_03
Patent number
US08673908B2

Reaction notes

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