Triethylamine → 2-(2-Methoxypyridin-3-yl)acetaldehyde

HRID 1837705Notes

Reaction equation

HRID 1837705 reaction equation
[CH3:1][O:2][C:3]1[C:8]([CH2:9][CH2:10][OH:11])=[CH:7][CH:6]=[CH:5][N:4]=1.C(N(CC)CC)C.C(=O)(O)[O-].[Na+]>CS(C)=O>[CH3:1][O:2][C:3]1[C:8]([CH2:9][CH:10]=[O:11])=[CH:7][CH:6]=[CH:5][N:4]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 140623082-(2-Methoxy-3-pyridinyl)ethanol

Product 1

HCID 226786312-(2-Methoxypyridin-3-yl)acetaldehydeYield 16.9%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

A solution of 2.7 g of pyridine-sulfur trioxide complex dissolved in DMSO was added dropwise at 20° C. or less to a solution of 1.2 g of 2-(2-methoxy-3-pyridyl)ethanol and 4.8 ml of triethylamine dissolved in DMSO. After stirring for 0.5 hour, a cooled sodium bicarbonate was added thereto, and the mixture was extracted with ethyl acetate. After drying over sodium sulfate, the solvent was evaporated. The residue was purified by silica gel chromatography (hexane:ethyl acetate=4:1), to give 200 mg of a yellow oil.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. dry with materialAfter drying over sodium sulfate
  3. customthe solvent was evaporated
  4. customThe residue was purified by silica gel chromatography (hexane:ethyl acetate=4:1)

Sources & evidence

ORD record
ord-c291d7359dc945199dd859cba9edd73b
Source dataset
uspto-grants-2004_08
Patent number
US06784192B2

Reaction notes

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