Water → 4-(2-(4-Formylphenyl)ethenyl)pyridine

HRID 636515Notes

Reaction equation

HRID 636515 reaction equation
[N:1]1[CH:6]=[CH:5][C:4](/[CH:7]=[CH:8]/[C:9]2[CH:16]=[CH:15][C:12]([CH2:13][OH:14])=[CH:11][CH:10]=2)=[CH:3][CH:2]=1.C(N(CC)CC)C.O>CS(C)=O>[N:1]1[CH:6]=[CH:5][C:4](/[CH:7]=[CH:8]/[C:9]2[CH:10]=[CH:11][C:12]([CH:13]=[O:14])=[CH:15][CH:16]=2)=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 962WaterHCID 8471TriethylamineHCID 70240750(4-(2-(Pyridin-4-YL)vinyl)phenyl)methanol

Product 1

HCID 53747304-(2-(4-Formylphenyl)ethenyl)pyridineYield 70.7%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of 4-[(E)-2-(4-pyridyl)vinyl]benzyl alcohol (740 mg) and triethylamine (1.77 g) in dimethyl sulfoxide (3 ml) was added sulfur trioxide—pyridine complex (1.11 g) at ambient temperature, and after stirring for 4 hours, water was added thereto. The mixture was extracted with ethyl acetate, and the extract was washed with water and brine, dried over magnesium sulfate and concentrated in vacuo. The residue was purified by flash chromatography (chloroform—ethyl acetate) and crystallized with diisopropyl ether to give 4-[(E)-2-(4-pyridyl)vinyl]-benzaldehyde (518 mg).

Workup

  1. extractionThe mixture was extracted with ethyl acetate
  2. washthe extract was washed with water and brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by flash chromatography (chloroform—ethyl acetate)
  6. customcrystallized with diisopropyl ether

Sources & evidence

ORD record
ord-e8e367e5e80e49d28f1041d9804717ab
Source dataset
uspto-grants-2001_02
Patent number
US06194396B1

Reaction notes

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