Sodium Methoxide → HCID 67056855, compound

HRID 1921278Notes

Reaction equation

HRID 1921278 reaction equation
[C:1]([NH:5]/[CH:6]=[C:7](\[C:14]([O:16][CH3:17])=[O:15])/[CH:8]=[CH:9]/[C:10]([O:12]C)=O)([CH3:4])([CH3:3])[CH3:2].[CH3:18][O-].[Na+]>CO>[C:1]([N:5]1[C:10](=[O:12])[CH:9]=[CH:8][C:7]([C:14]([O:16][CH2:17][CH3:18])=[O:15])=[CH:6]1)([CH3:2])([CH3:3])[CH3:4]

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 86639847HCID 86639847, compound

Product 1

HCID 67056855HCID 67056855, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a solution of dimethyl (2E,4Z)-4-[(tert-butylamino)methylene]-2-pentenedioate (1.2 g) in MeOH (10 mL) was added 28% sodium methoxide in MeOH (1.9 mL), and the mixture was heated to reflux for 8 hr under a nitrogen atmosphere. The solvent was evaporated in vacuo, and the residue was diluted with EtOAc (20 mL). The resulting mixture was washed successively with 1 M HCl (20 mL), saturated aqueous NaHCO3 (20 mL) and brine, dried over MgSO4 and evaporated in vacuo to give ethyl 1-(tert-butyl)-6-oxo-1,6-dihydro-3-pyridinecarboxylate (657 mg).

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 8 hr under a nitrogen atmosphere
  3. customThe solvent was evaporated in vacuo
  4. additionthe residue was diluted with EtOAc (20 mL)
  5. washThe resulting mixture was washed successively with 1 M HCl (20 mL), saturated aqueous NaHCO3 (20 mL) and brine
  6. dry with materialdried over MgSO4
  7. customevaporated in vacuo

Sources & evidence

ORD record
ord-79f622efa3af4a8f88cf1833c04524e0
Source dataset
uspto-grants-2012_05
Patent number
US08173684B2

Reaction notes

Loading…