Methanol → 3-Hydroxy-2-{1-(methoxycarbonyl)ethoxy}pyridine

HRID 1862263Notes

Reaction equation

HRID 1862263 reaction equation
C([O:4][C:5]1[C:6]([O:11][CH:12]([C:14]([O:16][CH3:17])=[O:15])[CH3:13])=[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][CH:12]([C:14]([O:16][CH3:17])=[O:15])[CH3:13])=[N:7][CH:8]=[CH:9][CH:10]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 11430Potassium CarbonateHCID 219335453-Acetoxy-2-{1-(methoxycarbonyl)ethoxy}pyridine

Product 1

HCID 219335243-Hydroxy-2-{1-(methoxycarbonyl)ethoxy}pyridineYield 67.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 0.34 g of 3-acetoxy-2-{1-(methoxycarbonyl)ethoxy}pyridine, 0.11 g of potassium carbonate and 2 ml methanol was stirred for 1 hour 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 190 mg of 3-hydroxy-2-{1-(methoxycarbonyl)ethoxy}pyridine.

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-fdb29fbebb364e8494fe7ae697ad9e06
Source dataset
uspto-grants-2003_03
Patent number
US06537948B1

Reaction notes

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