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

HRID 2214396Notes

Reaction equation

HRID 2214396 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 at room temperature for 3 hours. The reaction mixture was poured into water, and the mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate and then concentrated. The residue was subjected to silica gel column chromatography to give 73 mg of 3-hydroxy-2-(methoxycarbonyl)methoxypyridine.

Workup

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

Sources & evidence

ORD record
ord-c8c4423ab3bc4743add78780af7d1cc6
Source dataset
uspto-grants-2006_09
Patent number
US07109148B2

Reaction notes

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