Sodium hydride → HCID 18619139, compound

HRID 1862302Notes

Reaction equation

HRID 1862302 reaction equation
[H-].[Na+].Cl[C:4]1[CH:9]=[CH:8][C:7]([N+:10]([O-:12])=[O:11])=[CH:6][N:5]=1.[C:13]([O:17][CH3:18])(=[O:16])[CH2:14][OH:15]>O1CCCC1>[CH3:18][O:17][C:13]([CH2:14][O:15][C:4]1[CH:9]=[CH:8][C:7]([N+:10]([O-:12])=[O:11])=[CH:6][N:5]=1)=[O:16]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 66774Methyl GlycolateHCID 783082-Chloro-5-nitropyridine

Product 1

HCID 18619139HCID 18619139, compoundYield 77.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

1.26 g of sodium hydride was added to a mixture of 5.0 g of 2-chloro-5-nitropyridine, 3.13 g of methyl glycolate and 50 ml of tetrahydrofuran at 0° C. The mixture was stirred at 0° C. for 15 minutes, then at room temperature for 1 hour. 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 5.18 g of 2-(methoxycarbonyl)methoxy-5-nitropyridine.

Workup

  1. waitat room temperature for 1 hour
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-a626cc3737ad4c5097c6c1f3702c4e92
Source dataset
uspto-grants-2003_03
Patent number
US06537948B1

Reaction notes

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