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

HRID 1942260Notes

Reaction equation

HRID 1942260 reaction equation
[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][C:5]([CH2:9][OH:10])=[CH:4][N:3]=1>C(Cl)Cl.[O-2].[Mn+2]>[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][C:5]([CH:9]=[O:10])=[CH:4][N:3]=1

Participants

4

Reactant 1

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

Product 1

HCID 115356545,6-Dichloropyridine-3-carbaldehydeYield 90%

Reagents, catalysts & solvents 2

HCID 160959Manganese oxideCatalystHCID 6344DichloromethaneSolvent

Procedure

To a 500 mL round-bottom flask, manganese oxide (43.5 g, 0.50 mol) was added to a solution of 2,3-dichloro-5-hydroxylmethylpyridine (1, 8.10 g, 50.0 mMol) in anhydrous CH2Cl2 (150 mL). The resulting mixture was stirred at room temperature for 2 days, which was filtered through Celite and concentrated. The crude mixture was purified by a silica gel chromatography column eluting with a gradient of ethyl acetate (0-40%)/hexanes to give 7.2 g of the desired product 2 (90%). 1H NMR (400 MHz, CDCl3) δ 10.08 (1H, s), 8.77 (1H, d, J=1.97 Hz), 8.25 (1H, d, J=1.97 Hz). LC/MS (M+1): 176.

Workup

  1. filtrationwhich was filtered through Celite
  2. concentrationconcentrated
  3. customThe crude mixture was purified by a silica gel chromatography column
  4. washeluting with a gradient of ethyl acetate (0-40%)/hexanes

Sources & evidence

ORD record
ord-fa09d6d72af24696b9dae4826cafbc72
Source dataset
uspto-grants-2013_03
Patent number
US08389549B2

Reaction notes

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