Tetrahydrofuran → Ethyl 2-(3-nitropyridin-2-yl)oxyacetate

HRID 1862331Notes

Reaction equation

HRID 1862331 reaction equation
[H-].[Na+].Cl[C:4]1[C:9]([N+:10]([O-:12])=[O:11])=[CH:8][CH:7]=[CH:6][N:5]=1.[C:13]([O:17][CH2:18][CH3:19])(=[O:16])[CH2:14][OH:15].O1CCCC1>CN(C)C=O>[CH2:18]([O:17][C:13]([CH2:14][O:15][C:4]1[C:9]([N+:10]([O-:12])=[O:11])=[CH:8][CH:7]=[CH:6][N:5]=1)=[O:16])[CH3:19]

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 12184Ethyl GlycolateHCID 24758Sodium hydrideHCID 796132-Chloro-3-nitropyridine

Product 1

HCID 4425975Ethyl 2-(3-nitropyridin-2-yl)oxyacetateYield 85.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

11 g of sodium hydride was added to a mixture of 39.63 g of 2-chloro-3-nitropyridine, 31.23 g of ethyl glycolate, 250 ml of tetrahydrofuran and 20 ml of N,N-dimethylformamide at 0° C. The mixture was stirred at room temperature for 5 hours, then, the reaction solution was poured into ice 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 48.3 g of 2-(ethoxycarbonyl)methoxy-3-nitropyridine.

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-a4af2e54ae83403fae16651a5115369e
Source dataset
uspto-grants-2003_03
Patent number
US06537948B1

Reaction notes

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