HCID 19103184, compound → HCID 19103164, compound

HRID 1198738Notes

Reaction equation

HRID 1198738 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 ). 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-4273e5f7141c49558d8446e4508cfd3d
Source dataset
uspto-grants-1994_01
Patent number
US05281719

Reaction notes

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