Water → 5-(Dimethoxymethyl)picolinaldehyde

HRID 1281144Notes

Reaction equation

HRID 1281144 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([CH:8]([O:11][CH3:12])[O:9][CH3:10])=[CH:4][N:3]=1.C([Mg]Cl)(C)C.CN(C)[CH:20]=[O:21].O>O1CCCC1>[CH3:10][O:9][CH:8]([O:11][CH3:12])[C:5]1[CH:6]=[CH:7][C:2]([CH:20]=[O:21])=[N:3][CH:4]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6228DimethylformamideHCID 64252132-Bromo-5-(dimethoxymethyl)pyridineHCID 178418918HCID 178418918, compound

Product 1

HCID 184267805-(Dimethoxymethyl)picolinaldehydeYield 44.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-bromo-5-dimethoxymethylpyridine (1.19 g, 5.13 mmol) in tetrahydrofuran (8 mL) was added isopropylmagnesium chloride (2 mol/L in tetrahydrofuran; 4.2 mL, 8.4 mmol) under nitrogen atmosphere, and the mixture was stirred at room temperature for 3 h. Dimethylformamide (0.774 mL, 10.3 mmol) was added, and the mixture was stirred for additional 10 min. Water was added, and the mixture was extracted with ethyl acetate twice. The organic layer was washed with brine and dried on anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (5:1 to 3:1 hexane/ethyl acetate) to afford 5-dimethoxymethyl-2-pyridinecarboxaldehyde (413 mg, 44%).

Workup

  1. stirringthe mixture was stirred for additional 10 min
  2. extractionthe mixture was extracted with ethyl acetate twice
  3. washThe organic layer was washed with brine
  4. dry with materialdried on anhydrous sodium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. customthe residue was purified by silica gel column chromatography (5:1 to 3:1 hexane/ethyl acetate)

Sources & evidence

ORD record
ord-9e8dca299e84413fafc408b49443f0d6
Source dataset
uspto-grants-2002_09
Patent number
US06452014B1

Reaction notes

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