(5,6-Dichloropyridin-3-yl)methanol → 5,6-Dichloropyridine-3-carbaldehyde

HRID 130895Notes

Reaction equation

HRID 130895 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:9][OH:10])[CH:5]=[N:6][C:7]=1[Cl:8]>C(Cl)Cl.[O-2].[O-2].[Mn+4]>[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]=[O:10])[CH:5]=[N:6][C:7]=1[Cl:8]

Participants

4

Reactant 1

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

Product 1

HCID 115356545,6-Dichloropyridine-3-carbaldehydeYield 48%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

Combine (5,6-dichloro-pyridin-3-yl)-methanol (3.05 g, 17.11 mmol) and manganese dioxide (37.2 g, 427.9 mmol) in CH2Cl2 (25 mL). Stir the reaction mixture at rt overnight. Filter the reaction mixture through Celite® washing with CH2Cl2 (2×10 mL). Concentrate the filtrate and dry under vacuum to provide the title compound (1.44 g, 48%).

Workup

  1. filtrationFilter the reaction mixture through Celite®
  2. washwashing with CH2Cl2 (2×10 mL)
  3. concentrationConcentrate the filtrate
  4. customdry under vacuum

Sources & evidence

ORD record
ord-1eedb8e0688043248b814c4e9ca0649d
Source dataset
uspto-grants-2008_06
Patent number
US07381719B2

Reaction notes

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