Acetic Acid → HCID 67299891, compound

HRID 1260325Notes

Reaction equation

HRID 1260325 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][N:5]=1)(=[O:3])[CH3:2].[C:10](OCC)(=[O:16])[C:11]([O:13][CH2:14][CH3:15])=[O:12].CC[O-].[Na+].C(O)(=O)C>C(OCC)C.O>[CH2:14]([O:13][C:11](=[O:12])[C:10](=[O:16])/[CH:2]=[C:1](\[OH:3])/[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][N:5]=1)[CH3:15]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 7268Diethyl OxalateHCID 142862-AcetylpyridineHCID 2723922Sodium ethoxide

Product 1

HCID 67299891HCID 67299891, compoundYield 44.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

A solution of 2-acetylpyridine (5.0 g, 40 mmol) and diethyl oxalate (5.9 g, 40 mmol) in diethylether (75 ml) was cooled to 0° C. and treated with sodium ethylate (16.6 ml, 21% solution in ethanol). While stirring overnight, the reaction mixture was allowed to warm-up slowly to ambient temperature. The reaction mixture was acidified with acetic acid, diluted with water and extracted with diethylether. The combined organic phases were washed with water and brine, dried and evaporated. The isolated residue was triturated with heptane (30 ml) and diethylether (5 ml) for 2 h and the resulting suspension was filtrated to collect the product. This process was repeated to obtain the product as light brown solid (3.96 g, 44%). MS: M=220.1 (M−H)−

Workup

  1. extractionextracted with diethylether
  2. washThe combined organic phases were washed with water and brine
  3. customdried
  4. customevaporated
  5. customThe isolated residue was triturated with heptane (30 ml) and diethylether (5 ml) for 2 h
  6. filtrationthe resulting suspension was filtrated
  7. customto collect the product

Sources & evidence

ORD record
ord-79a9b62a02774444927ec7eba59cd502
Source dataset
uspto-grants-2013_06
Patent number
US08470820B2

Reaction notes

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