(6-(2-Methoxyethoxy)pyridin-3-yl)methanol → 6-(2-Methoxyethoxy)nicotinaldehyde

HRID 2371173Notes

Reaction equation

HRID 2371173 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][O:5][C:6]1[N:11]=[CH:10][C:9]([CH2:12][OH:13])=[CH:8][CH:7]=1>C1(C)C=CC=CC=1.O=[Mn]=O>[CH3:1][O:2][CH2:3][CH2:4][O:5][C:6]1[CH:7]=[CH:8][C:9]([CH:12]=[O:13])=[CH:10][N:11]=1

Participants

4

Reactant 1

HCID 15067095(6-(2-Methoxyethoxy)pyridin-3-yl)methanol

Product 1

HCID 150670976-(2-Methoxyethoxy)nicotinaldehydeYield 82.8%

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 1140TolueneSolvent

Procedure

[6-(2-methoxyethoxy)pyridine-3-yl]methanol (1.83 g 10.0 mmol) was dissolved in toluene (50 ml) and heated to reflux under an air condenser. Finely powdered MnO2 (4.0 g) was added portion wise over 2 hours. After a further 2 and a half hours of heating the mixture was taken off the boil allowed to cool slightly then filtered through celite and washed with toluene. The filtrate was concentrated in-vacuo to yield a pale yellow oil which crystallized under high vacuum to yield the crude product (1.50 g).

Workup

  1. temperatureheated
  2. temperatureto reflux under an air condenser
  3. temperatureAfter a further 2 and a half hours of heating the mixture
  4. temperatureto cool slightly
  5. filtrationthen filtered through celite
  6. washwashed with toluene
  7. concentrationThe filtrate was concentrated in-vacuo
  8. customto yield a pale yellow oil which
  9. customcrystallized under high vacuum

Sources & evidence

ORD record
ord-dc0cb038d31b4e628333093b0597dece
Source dataset
uspto-grants-2014_04
Patent number
US08710224B2

Reaction notes

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