Ethyl benzoylacetate → HCID 20156557, compound

HRID 986797Notes

Reaction equation

HRID 986797 reaction equation
[C:1]([CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Na].[CH:16]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=1)=[CH2:17]>Cl>[CH2:13]([O:12][C:10](=[O:11])[CH:9]([C:1](=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[CH2:17][CH2:16][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=1)[CH3:14]

Participants

5

Reactant 3

HCID 7170Ethyl benzoylacetateHCID 75212-VinylpyridineHCID 5360545Sodium

Product 1

HCID 20156557HCID 20156557, compoundYield 90.5%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A sample of 120 g (0.62 mole) of ethyl benzoylacetate was added to 1.44 g (0.062 mole) of sodium and 32.8 g (0.31 mole) of 2-vinylpyridine added under an atmosphere of nitrogen. The mixture was heated with mechanical stirring on the steam bath for 17 h. After cooling the reaction mixture to room temperature, 100 mL of 3N hydrochloric acid was added, and the aqueous mixture washed with ether. The hydrochloric acid layer was made basic with 10% potassium carbonate solution, and extracted with ether. The ether layer was washed with brine, dried (MgSO4), and the ether evaporated in vacuo to give 83.4 g (90% yield) of the crude title compound as a red oil.

Workup

  1. additionadded under an atmosphere of nitrogen
  2. temperatureThe mixture was heated
  3. washthe aqueous mixture washed with ether
  4. extractionextracted with ether
  5. washThe ether layer was washed with brine
  6. dry with materialdried (MgSO4)
  7. customthe ether evaporated in vacuo

Sources & evidence

ORD record
ord-f89c717ba3b648d39b8aa65770dadf93
Source dataset
uspto-grants-1987_12
Patent number
US04716172

Reaction notes

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