Acetic Acid → Ethyl 2-(4-pyridylmethyl)acetoacetate

HRID 1671495Notes

Reaction equation

HRID 1671495 reaction equation
[C:1]([O:7][CH2:8][CH3:9])(=[O:6])[CH2:2][C:3]([CH3:5])=[O:4].[N:10]1[CH:15]=[CH:14][C:13]([CH:16]=O)=[CH:12][CH:11]=1.N1CCCCC1.CC(O)=O>C(Cl)Cl>[N:10]1[CH:15]=[CH:14][C:13]([CH2:16][CH:2]([C:3]([CH3:5])=[O:4])[C:1]([O:7][CH2:8][CH3:9])=[O:6])=[CH:12][CH:11]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 8082PiperidineHCID 8868Ethyl AcetoacetateHCID 133894-Pyridinecarboxaldehyde

Product 1

HCID 10680502Ethyl 2-(4-pyridylmethyl)acetoacetateYield 90.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Ethyl acetoacetate (5.20 g), piridine-4-aldehyde (4.28 g), piperidine (0.4 ml) and AcOH (0.24 ml) are mixed in CH2Cl2 (150 ml) at room temperature under nitrogen atmosphere. The reaction mixture is stirred overnight and the solvent is removed. The residue is dissolved in EtOH (150 ml). 10% Pd/C (1.0 g) is added and reaction mixture is stirred at room temperature under hydrogen for 7 hours. Concentration under reduced pressure after Celite® filtration afford Ethyl 2-(4-piridylmethyl)acetoacetate (8.0 g) as colorless oil.

Workup

  1. customthe solvent is removed
  2. dissolutionThe residue is dissolved in EtOH (150 ml)
  3. addition10% Pd/C (1.0 g) is added
  4. customreaction mixture
  5. stirringis stirred at room temperature under hydrogen for 7 hours
  6. concentrationConcentration under reduced pressure
  7. filtrationafter Celite® filtration

Sources & evidence

ORD record
ord-e278aba6472f422bbded19172cbee8c4
Source dataset
uspto-grants-2011_08
Patent number
US07994318B2

Reaction notes

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