Sodium hydride → HCID 57833537, compound

HRID 2244149Notes

Reaction equation

HRID 2244149 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:6][CH:5]=1)([O-:3])=[O:2].[H-].[Na+].F[C:19]1[CH:24]=[CH:23][N:22]=[C:21]([C:25]([F:28])([F:27])[F:26])[CH:20]=1>CN(C=O)C>[CH2:14]([O:13][C:11](=[O:12])[CH:10]([C:7]1[CH:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:9][CH:8]=1)[C:19]1[CH:24]=[CH:23][N:22]=[C:21]([C:25]([F:28])([F:27])[F:26])[CH:20]=1)[CH3:15]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 79517Ethyl 4-nitrophenylacetateHCID 448914964-Fluoro-2-(trifluoromethyl)pyridine

Product 1

HCID 57833537HCID 57833537, compoundYield 41.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of ethyl (4-nitrophenyl)acetate (760 mg, 3.6 mmol) in DMF (10 mL) was added 60% sodium hydride (145 mg, 3.6 mmol). The deep purple reaction mixture was stirred at rt for 30 min, then 4-fluoro-2-trifluoromethyl-pyridine (500 mg, 3.0 mmol) was added. After heating at 70° C. for 2 h, the mixture was poured onto ice water and extracted with ethyl acetate. The organic layers were washed with water and brine, then dried over sodium sulfate and concentrated in vacuo. The residue was purified by column chromatography, eluting with 10-30% ethyl acetate in hexanes, to give (4-nitro-phenyl)-(2-trifluoromethyl-pyridin-4-yl)-acetic acid ethyl ester as a viscous yellow oil (440 mg, 41%).

Workup

  1. temperatureAfter heating at 70° C. for 2 h
  2. additionthe mixture was poured onto ice water
  3. extractionextracted with ethyl acetate
  4. washThe organic layers were washed with water and brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by column chromatography
  8. washeluting with 10-30% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-ce9517ba27ab448288e0c67a1d6d48d7
Source dataset
uspto-grants-2010_03
Patent number
US07678804B2

Reaction notes

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