3-Hydroxypyridine → Methyl 2-(pyridin-3-yloxy)acetate

HRID 1251464Notes

Reaction equation

HRID 1251464 reaction equation
[OH:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][CH:7]=1.[H-].[Na+].Br[CH2:11][C:12]([O:14][CH3:15])=[O:13]>CN(C=O)C>[N:4]1[CH:5]=[CH:6][CH:7]=[C:2]([O:1][CH2:11][C:12]([O:14][CH3:15])=[O:13])[CH:3]=1

Participants

5

Reactant 3

HCID 79713-HydroxypyridineHCID 24758Sodium hydrideHCID 60984Methyl bromoacetate

Product 1

HCID 23008475Methyl 2-(pyridin-3-yloxy)acetateYield 19.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 3-hydroxypyridine(5 g) in DMF(50 ml) was added slowly sodium hydride(2.1 g) under ice cooling. After the addition was completed, the reaction mixture was warmed up to room temperature and stirred at the same temperature for 30 minutes. The mixture was cooled with ice and methyl bromoacetate (8.1 g) was added slowly. After the addition was completed, the reaction mixture was stirred at room temperature for 15 hours and poured into ice water. The product was extracted with ethyl acetate, washed with brine, dried(MgSO4) and evaporated to dryness. The residue was purified by column chromatography on silica gel (chloroform: methanol=20:3) to obtain methyl 2-(3-pyridyloxy)acetate(1.7 g).

Workup

  1. additionAfter the addition
  2. additionwas added slowly
  3. additionAfter the addition
  4. stirringthe reaction mixture was stirred at room temperature for 15 hours
  5. extractionThe product was extracted with ethyl acetate
  6. washwashed with brine, dried(MgSO4)
  7. customevaporated to dryness
  8. customThe residue was purified by column chromatography on silica gel (chloroform: methanol=20:3)

Sources & evidence

ORD record
ord-64a58730c8a1441b84ac8c133cead51e
Source dataset
uspto-grants-2002_01
Patent number
US06342516B1

Reaction notes

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