Methanol → HCID 58105221, compound

HRID 1172244Notes

Reaction equation

HRID 1172244 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-013b11c4c2f34c159f966aa3a313720a
Source dataset
uspto-grants-2010_11
Patent number
US07834002B2

Reaction notes

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