Sodium Hydroxide → HCID 15462808, compound

HRID 1421255Notes

Reaction equation

HRID 1421255 reaction equation
[CH3:1][O:2][C:3]1[CH:18]=[CH:17][C:6]([CH2:7][CH:8](C(=O)C)[C:9]([O:11][CH2:12][CH3:13])=[O:10])=[CH:5][CH:4]=1.[OH-].[Na+].[Cl-].[N:22]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1[N+:28]#N>CCOC(C)=O>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([C:7]2[C:24]3[C:23](=[N:22][CH:27]=[CH:26][CH:25]=3)[NH:28][C:8]=2[C:9]([O:11][CH2:12][CH3:13])=[O:10])=[CH:17][CH:18]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 12248936Ethyl α-acetyl-4-methoxybenzenepropanoateHCID 14935597HCID 14935597, compound

Product 1

HCID 15462808HCID 15462808, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of ethyl 2-(4-methoxybenzyl)-3-oxobutyrate in EtOAc stirred at ice bath temperature under an argon atmosphere is added an aquious solution of NaOH. This is immediately followed by the addition of an aqueous solution of pyrid-2-yldiazonium chloride [prepared from 2-aminopyridine in 6 N HCl and NaNO2 ]. The mixture is partitioned between EtOAc and H2O. The aqueous layer is washed with EtOAc. The combined organic extracts are washed with saturated aqueous NaCl solution, dried (Na2SO4) and the solvent is removed in vacuo. The residue is dissolved in EtOH and the solution is saturated with HCl gas. This is refluxed then cooled to room temperature and partitioned EtOAc and saturated aqueous NaHCO3 solution. The aqueous layer is washed with EtOAc. The combined organic extract is washed with H2O then saturated aqueous NaCl solution, dried (Na2SO4) and the solvent is removed in vacuo. The residue is purified by chromatography to afford the title compound.

Workup

  1. customThe mixture is partitioned between EtOAc and H2O
  2. washThe aqueous layer is washed with EtOAc
  3. washThe combined organic extracts are washed with saturated aqueous NaCl solution
  4. dry with materialdried (Na2SO4)
  5. customthe solvent is removed in vacuo
  6. dissolutionThe residue is dissolved in EtOH
  7. temperatureThis is refluxed
  8. custompartitioned EtOAc and saturated aqueous NaHCO3 solution
  9. washThe aqueous layer is washed with EtOAc
  10. extractionThe combined organic extract
  11. washis washed with H2O
  12. dry with materialsaturated aqueous NaCl solution, dried (Na2SO4)
  13. customthe solvent is removed in vacuo
  14. customThe residue is purified by chromatography

Sources & evidence

ORD record
ord-f6a3bb367e1f4805b400255ed705eb48
Source dataset
uspto-grants-2000_06
Patent number
US06075037

Reaction notes

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