Methanol → HCID 58105221, compound

HRID 1668522Notes

Reaction equation

HRID 1668522 reaction equation
C([O:4][CH2:5][C:6]1[N:11]=[C:10]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH:9]=[CH:8][CH:7]=1)(=O)C.C(=O)([O-])[O-].[K+].[K+].CO>O>[OH:4][CH2:5][C:6]1[N:11]=[C:10]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH:9]=[CH:8][CH:7]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 11430Potassium CarbonateHCID 66853715HCID 66853715, compound

Product 1

HCID 58105221HCID 58105221, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 3.0 g of t-butyl 6-acetoxymethylpyridine-2-carboxylate were added 330 mg of potassium carbonate, 20 mL of methanol and 20 mL of water, and the mixture was stirred at room temperature for 3 hours. The methanol was removed under reduced pressure, then the residue was extracted with chloroform. The organic layer was washed with brine, dried over anhydrous magnesium sulfate, and the solvent was removed. The residue was purified by chromatography on silica gel (chloroform-ethanol 50:1) to give t-butyl 6-hydroxymethylpyridine-2-carboxylate as a yellow powder.

Workup

  1. customThe methanol was removed under reduced pressure
  2. extractionthe residue was extracted with chloroform
  3. washThe organic layer was washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customthe solvent was removed
  6. customThe residue was purified by chromatography on silica gel (chloroform-ethanol 50:1)

Sources & evidence

ORD record
ord-60838857266c4c7eb7e24479a56be8db
Source dataset
uspto-grants-2011_08
Patent number
US07989446B2

Reaction notes

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