Methyl iodide → 4-Methylpyridine-3-carbaldehyde

HRID 1957491Notes

Reaction equation

HRID 1957491 reaction equation
[Li]CCCC.C[N:7]([CH3:12])[CH2:8][CH2:9]NC.N1C=[CH:17][CH:16]=[C:15]([CH:19]=[O:20])C=1.IC>C1COCC1>[CH3:17][C:16]1[CH:9]=[CH:8][N:7]=[CH:12][C:15]=1[CH:19]=[O:20]

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 103713-PyridinecarboxaldehydeHCID 673381,2-Ethanediamine, N1,N1,N2-trimethyl-HCID 178418339Butyllithium2×

Product 1

HCID 124604704-Methylpyridine-3-carbaldehyde

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

n-BuLi (1.6 M in hexanes) (2.2 mmol, 1.37 ml) was added dropwise to a stirred solution of N,N,N'-trimethylethylenediamine (2.4 mmol, 0.245 g) in THF at -78° C. A solution of 3-pyridinecarboxaldehyde (2 mmol, 0.214 g) in THF was added and the mixture stirred for 15 min before adding a further portion of n-BuLi (1.6M in hexanes) (4 mmol, 2.5 ml). After stirring for 2 h at -70° C., iodomethane was added, the mixture stirred at RT for 30 min, then poured into aqueous NaCI solution, extracted twice with Et2O, dried (MgSO4), filtered and concentrated in vacuo. The residue was subjected to chromatography (SiO2 ; Et2O) to afford the title compound as an oil.

Workup

  1. stirringAfter stirring for 2 h at -70° C.
  2. stirringthe mixture stirred at RT for 30 min
  3. extractionextracted twice with Et2O
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-20083bae3d1a4ae5932f71f0c2c7ea0f
Source dataset
uspto-grants-1998_07
Patent number
US05786354

Reaction notes

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