Sodium Methoxide → HCID 67209425, compound

HRID 402506Notes

Reaction equation

HRID 402506 reaction equation
COC([C:5]1[C:10]([CH2:11][CH2:12][C:13]([O:15]C)=O)=[CH:9][C:8]([CH3:17])=[CH:7][N:6]=1)=O.C[O-].[Na+]>C1COCC1>[CH3:17][C:8]1[CH:9]=[C:10]2[CH2:11][CH2:12][C:13](=[O:15])[C:5]2=[N:6][CH:7]=1

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 67209404HCID 67209404, compound

Product 1

HCID 67209425HCID 67209425, compoundYield 117.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3-(2-Methoxycarbonyl-ethyl)-5-methyl-pyridine-2-carboxylic acid methyl ester (2.33 g, 9.82 mmol) was dissolved in THF (70 ml). NaOMe (0.796 g, 14.7 mmol) was added and the reaction was heated at reflux temperature for 2 h. The solvents were evaporated under reduced pressure. The residue was taken into 4.5 N aqueous hydrochloric acid (24 ml) and the mixture was heated at reflux temperature for 2 h. After cooling to it solid potassium carbonate was added carefully in portions until pH >8. The mixture was extracted with DCM, the combined organic layers were washed with aq Na2CO3 and aq ammonium chloride solution, dried over sodium sulfate, and the solvent was evaporated at reduced pressure. The residue was purified by chromatography on silica (Flashmaster, hes/EtOAc 1/1 to EtOAc over 15 min, EtOAc to EtOAc/MeOH 9/1 over 10 min) to obtain the product as off-white solid (1.7 g, 81%). [1H-NMR (DMSO-d6, 600 MHz) δ 8.57 (s, 1H), 7.87 (s, 1H), 3.06 (t, 2H), 2.65 (t, 2H), 2.42 (s, 3H); LCMS RtI=2.460 min; [M+H]+=148.0]

Workup

  1. temperaturethe reaction was heated
  2. temperatureat reflux temperature for 2 h
  3. customThe solvents were evaporated under reduced pressure
  4. temperaturethe mixture was heated
  5. temperatureat reflux temperature for 2 h
  6. temperatureAfter cooling to it solid potassium carbonate
  7. additionwas added carefully in portions until pH >8
  8. extractionThe mixture was extracted with DCM
  9. washthe combined organic layers were washed with aq Na2CO3 and aq ammonium chloride solution
  10. dry with materialdried over sodium sulfate
  11. customthe solvent was evaporated at reduced pressure
  12. customThe residue was purified by chromatography on silica (Flashmaster, hes/EtOAc 1/1 to EtOAc over 15 min, EtOAc to EtOAc/MeOH 9/1 over 10 min)

Sources & evidence

ORD record
ord-ba6809b560cb44b0bc87a052f28b6a33
Source dataset
uspto-grants-2014_06
Patent number
US08742106B2

Reaction notes

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