Sodium Hydroxide → 1-(4-Methoxypyridin-2-YL)ethan-1-OL

HRID 1789059Notes

Reaction equation

HRID 1789059 reaction equation
C([O:4][CH:5]([C:7]1[CH:12]=[C:11]([O:13][CH3:14])[CH:10]=[CH:9][N:8]=1)[CH3:6])(=O)C.[OH-].[Na+]>>[CH3:14][O:13][C:11]1[CH:10]=[CH:9][N:8]=[C:7]([CH:5]([OH:4])[CH3:6])[CH:12]=1

Participants

3

Reactant 2

HCID 14798Sodium HydroxideHCID 20189509(+)-1-[4-Methoxy-2-pyridyl]-ethyl acetate

Product 1

HCID 201895551-(4-Methoxypyridin-2-YL)ethan-1-OL

Conditions

Temperature
75 °C

Procedure

114 g of (+)-1-[4-methoxy-2-pyridyl]-ethyl acetate are added dropwise at 70° C. to 220 ml of 4N sodium hydroxide solution. The mixture is then stirred for a further 2 h at 75° C., cooled and extracted with four times 200 ml of dichloromethane. The organic phase is washed with 2N sodium hydroxide solution and water, dried over sodium sulphate and concentrated to dryness. After thorough stirring with 250 ml of diisopropyl ether, this gives 64 g (72%) of the title compound of m.p. 92° C.

Workup

  1. temperaturecooled
  2. extractionextracted with four times 200 ml of dichloromethane
  3. washThe organic phase is washed with 2N sodium hydroxide solution and water
  4. dry with materialdried over sodium sulphate
  5. concentrationconcentrated to dryness
  6. stirringAfter thorough stirring with 250 ml of diisopropyl ether

Sources & evidence

ORD record
ord-30efe7987615405c8b41b1f3ee99935c
Source dataset
uspto-grants-1987_08
Patent number
US04686230

Reaction notes

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