1-Butanol → Diethyl 5-ethylpyridine-2,3-dicarboxylate

HRID 1709309Notes

Reaction equation

HRID 1709309 reaction equation
[NH2:1][CH:2]([C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH2:3][C:4]([O:6][CH2:7][CH3:8])=[O:5].[CH2:14]([C:16]([CH:18]=[CH2:19])=O)C.[CH2:20](O)CCC>C1(C)C=CC(S(O)(=O)=O)=CC=1>[CH2:16]([C:18]1[CH:19]=[C:3]([C:4]([O:6][CH2:7][CH3:8])=[O:5])[C:2]([C:9]([O:11][CH2:12][CH3:13])=[O:10])=[N:1][CH:20]=1)[CH3:14]

Participants

5

Reactant 3

HCID 2631-ButanolHCID 153941-Penten-3-oneHCID 423728Aspartic acid, 1,4-diethyl ester

Product 1

HCID 10857926Diethyl 5-ethylpyridine-2,3-dicarboxylateYield 84.6%

Reagents, catalysts & solvents 1

HCID 6101p-Toluenesulfonic acidCatalyst

Procedure

Diethyl 1-amino-1,2-ethylenedicarboxylate (1.7 g) and α-ethylacrolein (0.84 g) are dissolved in n-butanol (10 ml), and thereto is added p-toluenesulfonic acid (35 mg). The mixture is refluxed for 15 hours (the degree of reaction of aminodiester is 97%). After distilling off the solvent, the residue is subjected to silica gel column chromatography, eluting with chloroform/methanol (1:0-1:0.01), to give diethyl 5-ethylpyridine-2,3-dicarboxylate (1.93 g., 84.6%). The product has a purity of 92.2% by liquid chromatographic analysis.

Workup

  1. temperatureThe mixture is refluxed for 15 hours (
  2. distillationAfter distilling off the solvent
  3. washeluting with chloroform/methanol (1:0-1:0.01)

Sources & evidence

ORD record
ord-7200b6c092f64fc292ebf0156c5189f2
Source dataset
uspto-grants-1990_08
Patent number
US04948896

Reaction notes

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