Sodium hydride → 1-Tert-butyl 3-ethyl 2-(6-nitropyridin-3-yl)malonate

HRID 1502101Notes

Reaction equation

HRID 1502101 reaction equation
[H-].[Na+].[C:3]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])(=[O:10])[CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6].Cl[C:17]1[CH:18]=[CH:19][C:20]([N+:23]([O-:25])=[O:24])=[N:21][CH:22]=1>CN(C=O)C>[N+:23]([C:20]1[N:21]=[CH:22][C:17]([CH:4]([C:5]([O:7][CH2:8][CH3:9])=[O:6])[C:3]([O:11][C:12]([CH3:14])([CH3:13])[CH3:15])=[O:10])=[CH:18][CH:19]=1)([O-:25])=[O:24]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 96345tert-Butyl ethyl malonateHCID 2598065-Chloro-2-nitropyridine

Product 1

HCID 673939371-Tert-butyl 3-ethyl 2-(6-nitropyridin-3-yl)malonate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
80 °C

Procedure

To a suspension of NaH (60% in oil, 0.650 g, 16.4 mmol) in DMF (40 mL) was added tert-butyl ethyl propanedioate (2.8 g, 15.1 mmol) at room temperature. The mixture was stirred for 30 min. A solution of 5-chloro-2-nitropyridine (2.00 g, 12.6 mmol) in DMF (10 mL) was added. The mixture was heated to 80° C. and stirred for 4 hours. The solvent was removed under reduce pressure. Water was added and the mixture was extracted with EtOAc. The combined organic layer was washed with brine, dried over anhydrous Na2SO4, concentrated and the residue was purified by column chromatography with silica gel to give tert-butyl ethyl (6-nitropyridin-3-yl)propanedioate.

Workup

  1. stirringstirred for 4 hours
  2. customThe solvent was removed
  3. additionWater was added
  4. extractionthe mixture was extracted with EtOAc
  5. washThe combined organic layer was washed with brine
  6. dry with materialdried over anhydrous Na2SO4
  7. concentrationconcentrated
  8. customthe residue was purified by column chromatography with silica gel

Sources & evidence

ORD record
ord-0b584c52a846479b91adf288431e6289
Source dataset
uspto-grants-2015_12
Patent number
US09206199B2

Reaction notes

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