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

HRID 1038540Notes

Reaction equation

HRID 1038540 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 potassium carbonate (276 mg, 2.0 mmol), and the mixture was stirred at room temperature for 1 hour. The reaction solution was concentrated in vacuo, added 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 by 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 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 by silica-gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-441ad4058ef948ff80191d990a482bfd
Source dataset
uspto-grants-2013_10
Patent number
US08551985B2

Reaction notes

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