Acetic Acid → HCID 86602399, compound

HRID 2373211Notes

Reaction equation

HRID 2373211 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=O)=[CH:4][N:3]=1.[O:10]=[C:11]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14].CC(O)=O.N1CCCCC1>C1C=CC=CC=1.C([O-])(O)=O.[Na+]>[C:11](/[C:12](=[CH:6]/[C:5]1[CH:4]=[N:3][C:2]([Cl:1])=[CH:9][CH:8]=1)/[C:13]([O:15][CH2:16][CH3:17])=[O:14])(=[O:10])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 7170Ethyl benzoylacetateHCID 8082PiperidineHCID 27640536-Chloropyridine-3-carbaldehyde

Product 1

HCID 86602399HCID 86602399, compoundYield 90.5%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 516892Sodium BicarbonateSolvent

Procedure

A mixture of 6-chloronicotinaldehyde (1 g), ethyl 3-oxo-3-phenylpropanoate (1.36 g), AcOH (0.04 ml), piperidine (0.028 ml) in benzene (15 ml) was refluxed for 1.5 hours. After cooling, the reaction mixture was diluted with saturated aqueous NaHCO3 and extracted with EtOAc. The organic layer was washed with brine, dried over anhydrous MgSO4 and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel eluting with a mixture of EtOAc and n-hexane (1:2) to give ethyl (2Z)-2-benzoyl-3-(6-chloro-3-pyridyl)acrylate (2.018 g) as a yellow oil.

Workup

  1. temperaturewas refluxed for 1.5 hours
  2. temperatureAfter cooling
  3. extractionextracted with EtOAc
  4. washThe organic layer was washed with brine
  5. dry with materialdried over anhydrous MgSO4
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by flash column chromatography on silica gel eluting with a mixture of EtOAc and n-hexane (1:2)

Sources & evidence

ORD record
ord-1b427728eab846b392fa95e0c7cd1a62
Source dataset
uspto-grants-2008_12
Patent number
US07459451B2

Reaction notes

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