HCID 19103184, compound → HCID 19103164, compound

HRID 466627Notes

Reaction equation

HRID 466627 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:12]=[C:11]([C:13]([F:16])([F:15])[F:14])[N:10](O)[C:9]=2[C:18]([F:21])([F:20])[F:19])=[CH:4][CH:3]=1>[Zn].C(O)(=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:12]=[C:11]([C:13]([F:14])([F:15])[F:16])[NH:10][C:9]=2[C:18]([F:21])([F:19])[F:20])=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 19103184HCID 19103184, compound

Product 1

HCID 19103164HCID 19103164, compoundYield 94.3%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Procedure

Zinc dust (20 g, 0.3 mol) is added to a solution of 3-(p-chlorophenyl)-2,5-bis(trifluoromethyl)-1-hydroxypyrrole (7.5 g, 0.023 mol) and acetic acid (50 mL). The reaction mixture is refluxed for 1/2 hour, cooled to room temperature, filtered to remove solids, diluted with water and extracted with ether. The combined organic extracts are washed sequentially with water, sodium carbonate solution and brine, dried over anhydrous magnesium sulfate and concentrated in vacuo to give a pale red liquid (6.8 g). A portion of the red liquid (1.6 g) is chromatographed using silica gel and eluted with methylene chloride to give the title product as a colorless liquid (1.1 g). Identified by IR and NMR spectral analyses.

Workup

  1. temperatureThe reaction mixture is refluxed for 1/2 hour
  2. filtrationfiltered
  3. customto remove solids
  4. additiondiluted with water
  5. extractionextracted with ether
  6. washThe combined organic extracts are washed sequentially with water, sodium carbonate solution and brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-9f99a3bb9f094ca5a4eaea06bdc35399
Source dataset
uspto-grants-1992_10
Patent number
US05157047

Reaction notes

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