2,5-Hexanedione → HCID 67253060, compound

HRID 912559Notes

Reaction equation

HRID 912559 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 3h 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. custompartitioned between EtOAc and water
  2. customThe organic layer was separated
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by flash chromatography (SiO2)
  6. washeluting with EtOAc/Hex (0:100 to 10:90)

Sources & evidence

ORD record
ord-68dfce1464304c18862b68178b91b64c
Source dataset
uspto-grants-2011_09
Patent number
US08026237B2

Reaction notes

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