Water → 2-Methoxypyridine-4-carbaldehyde

HRID 709751Notes

Reaction equation

HRID 709751 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([CH2:9][OH:10])[CH:6]=[CH:5][N:4]=1.C(N(CC)CC)C.O>CS(C)=O>[CH3:1][O:2][C:3]1[CH:8]=[C:7]([CH:6]=[CH:5][N:4]=1)[CH:9]=[O:10]

Participants

5

Reactant 3

HCID 962WaterHCID 8471TriethylamineHCID 14462410(2-Methoxypyridin-4-yl)methanol

Product 1

HCID 27629962-Methoxypyridine-4-carbaldehydeYield 65.2%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of (2-methoxypyridin-4-yl)methanol (6.74 g) and triethylamine (67.5 mL) in DMSO (200 mL) was added sulfur trioxide pyridine complex (30.8 g), and the mixture was stirred at room temperature for 30 min. Water was added to the reaction mixture at room temperature, and the mixture was extracted with ethyl acetate. The extract was washed with water and saturated brine, and dried over anhydrous magnesium sulfate. After silica gel filtration, the solvent was evaporated under reduced pressure to give a crude product of the title compound (4.33 g) as a brown oil. This compound was used for the next step without further purification.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with water and saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationAfter silica gel filtration
  5. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-b923e923b9b042799ec2b54b18a13174
Source dataset
uspto-grants-2015_11
Patent number
US09181186B2

Reaction notes

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