Triacetoxyperiodinane → 1-(3-Methoxy-6-pyridin-4-yl-pyridazin-4-yl)-ethanone

HRID 1786687Notes

Reaction equation

HRID 1786687 reaction equation
[CH3:1][O:2][C:3]1[N:4]=[N:5][C:6]([C:12]2[CH:17]=[CH:16][N:15]=[CH:14][CH:13]=2)=[CH:7][C:8]=1[CH:9]([OH:11])[CH3:10].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C1=CC=CC=2)=O>C(Cl)Cl>[CH3:1][O:2][C:3]1[N:4]=[N:5][C:6]([C:12]2[CH:17]=[CH:16][N:15]=[CH:14][CH:13]=2)=[CH:7][C:8]=1[C:9](=[O:11])[CH3:10]

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 230925161-(3-Methoxy-6-pyridin-4-yl-pyridazin-4-yl)-ethanol

Product 1

HCID 230924691-(3-Methoxy-6-pyridin-4-yl-pyridazin-4-yl)-ethanoneYield 92%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 0.91 g 1-(3-methoxy-6-pyridin-4-yl-pyridazin-4-yl)-ethanol in 10 ml CH2Cl2 is added a suspension of 1.70 g Dess-Martin Periodane in 10 ml CH2Cl2 at room temperature. After being stirred for 3 h, the suspension is extracted with 5% aq. Na2S2O3 solution. The organic layer is washed with water, dried over MgSO4 and concentrated in vacuo. The residue is purified by chromatography to give 0.83 g (92%) of the desired product as a yellow solid.

Workup

  1. extractionthe suspension is extracted with 5% aq. Na2S2O3 solution
  2. washThe organic layer is washed with water
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated in vacuo
  5. customThe residue is purified by chromatography

Sources & evidence

ORD record
ord-fda2ba8339ae49b3950cb537d1f4f04f
Source dataset
uspto-grants-2009_03
Patent number
US07507734B2

Reaction notes

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