Methyl 3-oxovalerate → Methyl 2-ethyl-6-methylnicotinate

HRID 591492Notes

Reaction equation

HRID 591492 reaction equation
[C:1]([CH2:5][C:6]([O:8][CH3:9])=[O:7])(=O)[CH2:2][CH3:3].C[Si](C)(C)[C:12]#[C:13][C:14](=O)[CH3:15].C([O-])(=O)C.[NH4+:23]>CO>[CH2:2]([C:1]1[N:23]=[C:14]([CH3:15])[CH:13]=[CH:12][C:5]=1[C:6]([O:8][CH3:9])=[O:7])[CH3:3]

Participants

5

Reactant 3

HCID 121699Methyl 3-oxovalerateHCID 517165Ammonium AcetateHCID 27346644-(Trimethylsilyl)-3-butyn-2-one

Product 1

HCID 57561949Methyl 2-ethyl-6-methylnicotinate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

To a mixture of methyl propionylacetate (1.93 mL), 4-trimethylsilyl-3-butyn-2-one (2.65 mL) in MeOH (100 mL) was added ammonium acetate (3.55 g) at room temperature. The mixture was stirred at 60° C. overnight. After cooling, the mixture was concentrated. The residue was diluted with water, and the mixture was extracted with EtOAc. The organic layer was washed with brine, dried over MgSO4 and concentrated in vacuo. The residue was dissolved in EtOAc and the insoluble material was removed by filtration. The filtrate was concentrated and the residue was purified by silica gel column chromatography (NH, EtOAc/hexane) to give the title compound (1.56 g).

Workup

  1. temperatureAfter cooling
  2. concentrationthe mixture was concentrated
  3. additionThe residue was diluted with water
  4. extractionthe mixture was extracted with EtOAc
  5. washThe organic layer was washed with brine
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated in vacuo
  8. dissolutionThe residue was dissolved in EtOAc
  9. customthe insoluble material was removed by filtration
  10. concentrationThe filtrate was concentrated
  11. customthe residue was purified by silica gel column chromatography (NH, EtOAc/hexane)

Sources & evidence

ORD record
ord-52f2eeef99ec43d58e10a7cc82bb3316
Source dataset
uspto-grants-2016_01
Patent number
US09238639B2

Reaction notes

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