Triacetoxyperiodinane → 5,6-Dichloropyridine-3-carbaldehyde

HRID 1621383Notes

Reaction equation

HRID 1621383 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:9][OH:10])[CH:5]=[N:6][C:7]=1[Cl:8].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C([O-])(O)=O.[Na+].O.C(Cl)Cl>[Cl:1][C:2]1[C:7]([Cl:8])=[N:6][CH:5]=[C:4]([CH:3]=1)[CH:9]=[O:10]

Participants

6

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 21882961(5,6-Dichloropyridin-3-yl)methanol

Product 1

HCID 115356545,6-Dichloropyridine-3-carbaldehyde

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×HCID 516892Sodium BicarbonateSolvent

Procedure

A mixture of 5,6-dichloro-3-pyridinemethanol (2.9967 g, 16.8 mmol) in DCM (3.00 mL, 46.6 mmol) was treated with Dess-Martin periodinane (7.14 g, 16.8 mmol) at room temperature and the mixture was stirred at room temperature overnight. The resulting reaction mixture was diluted with NaHCO3 (aq) and water (5 mL each) and diluted with DCM (5 mL). The separated aqueous layer was extracted with DCM (2×10 mL) and the combined organic layers were washed with brine, dried over Na2SO4, and concentrated to give a pale-yellow solid which was used directly for the next step.

Workup

  1. customThe resulting reaction mixture
  2. extractionThe separated aqueous layer was extracted with DCM (2×10 mL)
  3. washthe combined organic layers were washed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. customto give a pale-yellow solid which

Sources & evidence

ORD record
ord-33b687437bb94f10b3a5aca3d759fe36
Source dataset
uspto-grants-2014_07
Patent number
US08772480B2

Reaction notes

Loading…