Water → HCID 18426857, compound

HRID 1281153Notes

Reaction equation

HRID 1281153 reaction equation
Br[C:2]1[C:7]([CH3:8])=[CH:6][C:5]([CH:9]([O:12][CH3:13])[O:10][CH3:11])=[C:4]([CH3:14])[N:3]=1.C([Li])CCC.CN(C)[CH:22]=[O:23].O>O1CCCC1>[CH3:11][O:10][CH:9]([O:12][CH3:13])[C:5]1[CH:6]=[C:7]([CH3:8])[C:2]([CH:22]=[O:23])=[N:3][C:4]=1[CH3:14]

Participants

6

Reactant 4

HCID 962WaterHCID 6228DimethylformamideHCID 18426828HCID 18426828, compoundHCID 178418339Butyllithium

Product 1

HCID 18426857HCID 18426857, compoundYield 35.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-bromo-5-dimethoxymethyl-3,6-dimethylpyridine (382 mg, 1.47 mmol) in tetrahydrofuran (6 mL) were added n-butyllithium (1.6 mol/L; 1,4 mL, 2.2 mmol) and dimethylformamide (0.23 mL, 3.0 mmol) sequentially at −78° C. under nitrogen atmosphere, and the mixture was stirred for 40 min. Water was added, and the mixture was extracted with ethyl acetate. The organic layer was combined, washed with brine and dried on anhydrous sodium sulfate. The solvent was removed under reduced pressure, and the residue was purified by column chromatography (6:1 hexane/ethyl acetate) to afford 5-dimethoxymetyl-3,6-dimethyl-2-pyridinecarboxaldehyde (109 mg, 35%).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washwashed with brine
  3. dry with materialdried on anhydrous sodium sulfate
  4. customThe solvent was removed under reduced pressure
  5. customthe residue was purified by column chromatography (6:1 hexane/ethyl acetate)

Sources & evidence

ORD record
ord-82e80bd92480409ab86906bdb2516259
Source dataset
uspto-grants-2002_09
Patent number
US06452014B1

Reaction notes

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