Sodium hydride → HCID 58413322, compound

HRID 532260Notes

Reaction equation

HRID 532260 reaction equation
[OH:1][CH:2]([CH3:9])[CH2:3][C:4]([O:6][CH2:7][CH3:8])=[O:5].[H-].[Na+].F[C:13]1[CH:18]=[C:17]([F:19])[CH:16]=[CH:15][C:14]=1[N+:20]([O-:22])=[O:21]>C1COCC1>[F:19][C:17]1[CH:16]=[CH:15][C:14]([N+:20]([O-:22])=[O:21])=[C:13]([CH:18]=1)[O:1][CH:2]([CH3:9])[CH2:3][C:4]([O:6][CH2:7][CH3:8])=[O:5]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 62572Ethyl 3-HydroxybutyrateHCID 679672,4-Difluoronitrobenzene

Product 1

HCID 58413322HCID 58413322, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Ethyl 3-Hydroxybutyrate (6.5 ml) was dissolved in THF (350.0 ml) at 0° C. and NaH (4.8 g) was added. The reaction was stirred at room temperature for 30 min. Then 5.5 g 2,4-difluoronitrobenzene was added and the mixture was heated at reflux overnight. The reaction was concentrated in vacuo and the residue was dissolved in water and dichloromethane. The organic layer was separated, dried and concentrated in vacuo. The residue was purified by chromatography (silica/dichloromethane) to yield the title compound.

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux overnight
  3. concentrationThe reaction was concentrated in vacuo
  4. dissolutionthe residue was dissolved in water
  5. customThe organic layer was separated
  6. customdried
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by chromatography (silica/dichloromethane)

Sources & evidence

ORD record
ord-5378a7c4eefe4640953be709f0fa83e7
Source dataset
uspto-grants-2014_10
Patent number
US08853193B2

Reaction notes

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