2,5-Hexanedione → HCID 67253060, compound

HRID 383728Notes

Reaction equation

HRID 383728 reaction equation
[F:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[C:4]([C:9]([F:12])([F:11])[F:10])[CH:3]=1.[CH3:13][C:14](=O)[CH2:15][CH2:16][C:17](=O)[CH3:18]>C(O)(=O)C>[F:1][C:2]1[CH:8]=[CH:7][C:5]([N:6]2[C:17]([CH3:18])=[CH:16][CH:15]=[C:14]2[CH3:13])=[C:4]([C:9]([F:10])([F:11])[F:12])[CH:3]=1

Participants

4

Reactant 2

HCID 80352,5-HexanedioneHCID 678534-Fluoro-2-(trifluoromethyl)aniline

Product 1

HCID 67253060HCID 67253060, compoundYield 50.6%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 4-fluoro-2-(trifluoromethyl)aniline (4.4 g, 24.6 mmol), 2,5-hexanedione (2.8 g, 24.5 mmol) and acetic acid (0.28 mL) was heated to 100° C. After 3 h the reaction mixture was cooled and partitioned between EtOAc and water. The organic layer was separated, dried (MgSO4), and concentrated in vacuo. The residue was purified by flash chromatography (SiO2), eluting with EtOAc/Hex (0:100 to 10:90) to afford 1-[4-fluoro-2-(trifluoromethyl)phenyl]-2,5-dimethyl-1H-pyrrole as a yellow oil (3.19 g, 50%); 1H NMR (CDCl3): δ 7.52 (dd, J=8, 3 Hz, 1H), 7.35 (dt, J=3, 8 Hz, 1H), 7.25 (dd, J=5, 8 Hz, 1H), 5.90 (s, 2H), 1.91 (s, 6H); MS (ESI) m/z 258 [M+H]+.

Workup

  1. temperatureAfter 3 h the reaction mixture was cooled
  2. custompartitioned between EtOAc and water
  3. customThe organic layer was separated
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by flash chromatography (SiO2)
  7. washeluting with EtOAc/Hex (0:100 to 10:90)

Sources & evidence

ORD record
ord-311d488e650541969023051d9dd4e682
Source dataset
uspto-grants-2013_02
Patent number
US08367667B2

Reaction notes

Loading…