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Acetic Acid → ethyl (2Z)-2-benzoyl-3-(5-methyl-3-pyridyl)acrylate

HRID 2373208
Notes
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Reaction equation

HRID 2373208 reaction equation
[CH3:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([CH:9]=1)[CH:7]=O.[C:10]([CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20])(=[O:17])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.CC(O)=O.N1CCCCC1>CCO>[C:10](/[C:18](=[CH:7]/[C:6]1[CH:5]=[N:4][CH:3]=[C:2]([CH3:1])[CH:9]=1)/[C:19]([O:21][CH2:22][CH3:23])=[O:20])(=[O:17])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 7170Ethyl benzoylacetateHCID 8082PiperidineHCID 141411585-Methylpyridine-3-carbaldehyde

Product 1

HCID 86602398ethyl (2Z)-2-benzoyl-3-(5-methyl-3-pyridyl)acrylateYield 101.1%

Reagents, catalysts & solvents 1

HCID 702
Ethanol
Solvent

Procedure

A mixture of 5-methylnicotinaldehyde (400 mg), ethyl benzoylacetate (635 mg), AcOH (0.15 ml), piperidine (0.15 ml) in EtOH (5 ml) was stirred at room temperature for 24 hours. After evaporation, the residue 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 to give ethyl (2Z)-2-benzoyl-3-(5-methyl-3-pyridyl)acrylate (986 mg) as a yellow oil.

Workup

  1. customAfter evaporation
  2. additionthe residue was diluted with saturated aqueous NaHCO3
  3. extractionextracted with EtOAc
  4. washThe organic layer was washed with brine
  5. dry with materialdried over anhydrous MgSO4
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-27d42d51e999429aac87dae60e9849ad
Source dataset
uspto-grants-2008_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07459451B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes