Methanol → Methyl 2-((3-hydroxypyridin-2-yl)oxy)acetate

HRID 1862247Notes

Reaction equation

HRID 1862247 reaction equation
C([O:4][C:5]1[C:6]([O:11][CH2:12][C:13]([O:15][CH3:16])=[O:14])=[N:7][CH:8]=[CH:9][CH:10]=1)(=O)C.C(=O)([O-])[O-].[K+].[K+].CO>O>[OH:4][C:5]1[C:6]([O:11][CH2:12][C:13]([O:15][CH3:16])=[O:14])=[N:7][CH:8]=[CH:9][CH:10]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 11430Potassium CarbonateHCID 121155133-Acetoxy-2-(methoxycarbonyl)methoxypyridine

Product 1

HCID 12115514Methyl 2-((3-hydroxypyridin-2-yl)oxy)acetateYield 89.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 0.1 g of 3-acetoxy-2-(methoxycarbonyl)methoxypyridine, 31 mg of potassium carbonate and 1 ml of methanol was stirred for 3 hours at room temperature. The reaction solution was poured into water, and extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, and concentrated. The residue was subjected to silica gel column chromatography to obtain 73 mg of 3-hydroxy-2-(methoxycarbonyl)methoxypyridine.

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-26707df87a8a4537912e0827f1d3d465
Source dataset
uspto-grants-2003_03
Patent number
US06537948B1

Reaction notes

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