Triacetoxyperiodinane → HCID 57515868, compound

HRID 1921943Notes

Reaction equation

HRID 1921943 reaction equation
[CH3:1][O:2][CH2:3][O:4][C:5]1[C:6]([CH:15]([OH:17])[CH3:16])=[CH:7][C:8]([C:11]([F:14])([F:13])[F:12])=[N:9][CH:10]=1.C([O-])(O)=O.[Na+].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)Cl>[CH3:1][O:2][CH2:3][O:4][C:5]1[C:6]([C:15](=[O:17])[CH3:16])=[CH:7][C:8]([C:11]([F:14])([F:12])[F:13])=[N:9][CH:10]=1

Participants

5

Reactant 3

HCID 159087TriacetoxyperiodinaneHCID 516892Sodium BicarbonateHCID 57515866HCID 57515866, compound

Product 1

HCID 57515868HCID 57515868, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred mixture of 1-(5-(methoxymethoxy)-2-(trifluoromethyl)pyridin-4-yl)ethanol (3.2 g, 13 mmol) and NaHCO3 (3.2 g, 38 mmol) in DCM (100 ml) was added Dess Martin Periodinane (5.9 g, 14 mmol). The reaction mixture was stirred at rt in 16 h, the solid was filtered, the filtrate was concentrated, then taken up and stirred in ether/EtOAc. The precipitated white solids were filtered and discarded. The filtrate was concentrated to give the title compound as a light yellow oil. MS (m+1): 250.2.

Workup

  1. filtrationthe solid was filtered
  2. concentrationthe filtrate was concentrated
  3. stirringstirred in ether/EtOAc
  4. filtrationThe precipitated white solids were filtered
  5. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-2b995f7885824544ab483b12da544ed6
Source dataset
uspto-grants-2012_05
Patent number
US08173810B2

Reaction notes

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