Dimethylformamide → 5-Methylpyridine-2-carbaldehyde

HRID 1791351Notes

Reaction equation

HRID 1791351 reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([Mg]Br)=[N:6][CH:7]=1.C1C[O:13][CH2:12]C1.CN(C=O)C>>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([CH:12]=[O:13])=[N:6][CH:7]=1

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 8028TetrahydrofuranHCID 178426145HCID 178426145, compound

Product 1

HCID 104643395-Methylpyridine-2-carbaldehydeYield 62.6%

Procedure

To the 0.25 M 5-methyl-2-pyridinylmagnesium bromide of THF solution (20 mL, 5 mmol), DMF (0.773 mL, 10 mmol) was added at room temperature under argon. The reaction mixture was stirred for 10 min. and concentrated in vacuo. The residue was quenched with saturated ammonium chloride and dichloromethane. The organic layer was dried and the product was purified by silica gel column chromatography with 20% ethyl acetate in hexanes to give 379 mg (62.6%) of the title compound. GC-MS (M+): 121.

Workup

  1. concentrationconcentrated in vacuo
  2. customThe residue was quenched with saturated ammonium chloride and dichloromethane
  3. customThe organic layer was dried
  4. customthe product was purified by silica gel column chromatography with 20% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-36199a77d7744869bd14dc8e316823d6
Source dataset
uspto-grants-2006_07
Patent number
US07074809B2

Reaction notes

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