Potassium Carbonate → [5-(Propan-2-yloxy)pyridin-2-yl]methanol

HRID 1690170Notes

Reaction equation

HRID 1690170 reaction equation
C([O:4][CH2:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][CH:13]([CH3:15])[CH3:14])=[CH:8][N:7]=1)(=O)C.C(=O)([O-])[O-].[K+].[K+]>CO>[CH3:15][CH:13]([O:12][C:9]1[CH:10]=[CH:11][C:6]([CH2:5][OH:4])=[N:7][CH:8]=1)[CH3:14]

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 66598252[5-(1-Methylethoxy)pyridin-2-yl]methyl acetate

Product 1

HCID 66598374[5-(Propan-2-yloxy)pyridin-2-yl]methanolYield 83%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

[5-(1-Methylethoxy)pyridin-2-yl]methyl acetate (209 mg) was dissolved in methanol (2.0 mL), added with potassium carbonate (276 mg, 2.0 mmol), and the resultant mixture was stirred at room temperature for 1 hour. The reaction solution was concentrated in vacuo, added with water, and extracted with ethyl acetate. The organic layer was washed with brine, dried over sodium sulfate, and concentrated in vacuo. The obtained residue was purified using silica-gel column chromatography (hexane/ethyl acetate) and [5-(1-methylethoxy)pyridin-2-yl]methanol (137 mg, yield 83%) was obtained as a yellow oil.

Workup

  1. concentrationThe reaction solution was concentrated in vacuo
  2. additionadded with water
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated in vacuo
  7. customThe obtained residue was purified

Sources & evidence

ORD record
ord-39bd6d0732094af0bac87ddc56d0d97f
Source dataset
uspto-grants-2012_04
Patent number
US08153634B2

Reaction notes

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