Sodium hydride → N-ethoxyethyl-2-trifluoroacetylpyrrole

HRID 1791017Notes

Reaction equation

HRID 1791017 reaction equation
[H-].[Na+].[F:3][C:4]([F:13])([F:12])[C:5]([C:7]1[NH:8][CH:9]=[CH:10][CH:11]=1)=[O:6].[CH2:14]([O:16][CH2:17][CH2:18]Br)[CH3:15]>CN(C=O)C>[CH2:14]([O:16][CH2:17][CH2:18][N:8]1[CH:9]=[CH:10][CH:11]=[C:7]1[C:5](=[O:6])[C:4]([F:3])([F:12])[F:13])[CH3:15]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 611412-Bromoethyl ethyl etherHCID 137637Ethanone, 2,2,2-trifluoro-1-(1H-pyrrol-2-yl)-

Product 1

HCID 68869870N-ethoxyethyl-2-trifluoroacetylpyrrole

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

To a suspension of 268 mg (6.70 mmol) of NaH (60% dispersion in oil) in 20 mL DMF at 0° C. was added 1.01 g (6.19 mmol) of 2-(trifluoroacteyl)pyrrole and the mixture was stirred at 0° C. for 1 h. After this time, 765 μL (6.51 mmol) of 2-bromoethyl ethyl ether was added and the mixture was warmed to 60° C. and stirred for 16 h. After this time, the reaction mixture was allowed to cool to room temperature, quenched by the addition of a saturated aqueous solution of ammonium chloride, and extracted with EtOAc. The organic layer was washed with water and brine, dried over Na2SO4, filtered and the filtrate was concentrated. The residue was purified by chromatography on silica gel (pure hexanes grading to hexanes:EtOAc, 97:3) to give the title compound.

Workup

  1. temperaturethe mixture was warmed to 60° C.
  2. stirringstirred for 16 h
  3. temperatureto cool to room temperature
  4. customquenched by the addition of a saturated aqueous solution of ammonium chloride
  5. extractionextracted with EtOAc
  6. washThe organic layer was washed with water and brine
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. concentrationthe filtrate was concentrated
  10. customThe residue was purified by chromatography on silica gel (pure hexanes grading to hexanes:EtOAc, 97:3)

Sources & evidence

ORD record
ord-c9e8b955dadb4be390e459aed7fa1256
Source dataset
uspto-grants-2006_07
Patent number
US07071358B2

Reaction notes

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