3,4-dihydro-2H-pyrano[2,3-c]pyridin-6-ylmethanol → 3,4-dihydro-2H-pyrano[2,3-c]pyridine-6-carbaldehyde

HRID 385565Notes

Reaction equation

HRID 385565 reaction equation
[O:1]1[C:6]2=[CH:7][N:8]=[C:9]([CH2:11][OH:12])[CH:10]=[C:5]2[CH2:4][CH2:3][CH2:2]1>C(Cl)(Cl)Cl.[O-2].[O-2].[Mn+4]>[O:1]1[C:6]2=[CH:7][N:8]=[C:9]([CH:11]=[O:12])[CH:10]=[C:5]2[CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 1

HCID 223133613,4-dihydro-2H-pyrano[2,3-c]pyridin-6-ylmethanol

Product 1

HCID 566403113,4-dihydro-2H-pyrano[2,3-c]pyridine-6-carbaldehydeYield 97.2%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6212ChloroformSolvent

Procedure

To a solution of 0.25 g of (3,4-dihydro-2H-pyrano(2,3-c)pyridin-6-yl)methanol in 7.5 mL of chloroform, 0.66 g of manganese dioxide was added, and the mixture was heated under reflux while stirring for 4 hours 50 minutes. The reaction mixture was cooled to room temperature, the insoluble substance was then filtered off, and the solvent was distilled off under reduced pressure to obtain 0.24 g of 3,4-dihydro-2H-pyrano(2,3-c)pyridine-6-carbaldehyde as a light yellow oily substance.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux
  3. filtrationthe insoluble substance was then filtered off
  4. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-42bb9524deb642bc8debad7f04403bb2
Source dataset
uspto-grants-2013_02
Patent number
US08367831B2

Reaction notes

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