Triacetoxyperiodinane → 2,2-Dimethyl-3-(4-pyridin-3-yl-imidazol-1-yl)-propioaldehyde

HRID 432573Notes

Reaction equation

HRID 432573 reaction equation
[CH3:1][C:2]([CH3:17])([CH2:5][N:6]1[CH:10]=[C:9]([C:11]2[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=2)[N:8]=[CH:7]1)[CH2:3][OH:4].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.C([O-])(O)=O.[Na+]>C(Cl)Cl>[CH3:1][C:2]([CH3:17])([CH2:5][N:6]1[CH:10]=[C:9]([C:11]2[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=2)[N:8]=[CH:7]1)[CH:3]=[O:4]

Participants

5

Reactant 3

HCID 159087TriacetoxyperiodinaneHCID 516892Sodium BicarbonateHCID 187597722,2-Dimethyl-3-(4-pyridin-3-yl-imidazol-1-yl)-propanol

Product 1

HCID 187597702,2-Dimethyl-3-(4-pyridin-3-yl-imidazol-1-yl)-propioaldehyde

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2,2-Dimethyl-3-(4-pyridin-3-yl-imidazol-1-yl)-propanol (11 mg) in CH2Cl2 was added Dess-Martin periodinane (41 mg) and the resulting solution was stirred at room temperature for 15 minutes. Saturated NaHCO3 was added, the aqueous layer was extracted with CHCl3, the combined organic layers were washed with brine, dried over Na2SO4 and evaporated in vacuo to afford the title compound as a slightly yellow oil.

Workup

  1. extractionthe aqueous layer was extracted with CHCl3
  2. washthe combined organic layers were washed with brine
  3. dry with materialdried over Na2SO4
  4. customevaporated in vacuo

Sources & evidence

ORD record
ord-324e5c4dc50846dbadca52ec4dc1eecf
Source dataset
uspto-grants-2003_12
Patent number
US06664238B1

Reaction notes

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