Sodium hydride → HCID 53818427, compound

HRID 1372565Notes

Reaction equation

HRID 1372565 reaction equation
[H-].[Na+].[C:3]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])(=[O:12])[CH2:4][C:5]([O:7][C:8]([CH3:11])([CH3:10])[CH3:9])=[O:6].[H][H].[F:20][C:21]1[C:22]([N+:30]([O-:32])=[O:31])=[C:23]([O:28][CH3:29])[CH:24]=[C:25](F)[CH:26]=1>CN(C=O)C.O>[F:20][C:21]1[CH:26]=[C:25]([CH:4]([C:5]([O:7][C:8]([CH3:9])([CH3:10])[CH3:11])=[O:6])[C:3]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH:24]=[C:23]([O:28][CH3:29])[C:22]=1[N+:30]([O-:32])=[O:31]

Participants

7

Reactant 4

HCID 24758Sodium hydrideHCID 68324Di-tert-butyl malonateHCID 103301291,5-Difluoro-3-methoxy-2-nitrobenzeneHCID 178418361HCID 178418361, compound

Product 1

HCID 53818427HCID 53818427, compoundYield 62%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Conditions

Temperature
0 °C

Procedure

In DMF (60 ml) was suspended sodium hydride (2.75 g, 68.7 mmol). Under stirring at 0° C., di-tert-butyl malonate (14.9 g, 68.7 mmol) was added dropwise. After vigorous emission of a hydrogen gas stopped, a solution of 3,5-difluoro-2-nitroanisole (5.20 g, 27.5 mmol) in DMF (40 ml) was added. The reaction mixture was stirred at 80° C. for 4 hours. After cooling the reaction mixture to room temperature, water (200 ml) was added to terminate the reaction, followed by extraction with ether (300 ml). The extract was washed with saturated brine (200 ml), dried over anhydrous magnesium sulfate and distilled reduced pressure to remove the solvent. The residue was purified by chromatography on a silica gel column, whereby hexane-ethyl acetate (10:1) eluate fractions, the title compound (6.56 g, 62%) was obtained as an yellow oil.

Workup

  1. stirringThe reaction mixture was stirred at 80° C. for 4 hours
  2. temperatureAfter cooling the reaction mixture to room temperature
  3. customto terminate
  4. customthe reaction
  5. extractionfollowed by extraction with ether (300 ml)
  6. washThe extract was washed with saturated brine (200 ml)
  7. dry with materialdried over anhydrous magnesium sulfate
  8. distillationdistilled reduced pressure
  9. customto remove the solvent
  10. customThe residue was purified by chromatography on a silica gel column, whereby hexane-ethyl acetate (10:1) eluate fractions

Sources & evidence

ORD record
ord-96420fece82d4af8aacf88b687f54af4
Source dataset
uspto-grants-2007_01
Patent number
US07157487B2

Reaction notes

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