Potassium Iodide → HCID 14349144, compound

HRID 414851Notes

Reaction equation

HRID 414851 reaction equation
Cl[CH2:2][C:3]1[CH:12]=[CH:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]=1.[F:13][C:14]([F:28])([F:27])[CH2:15][CH2:16][CH2:17][C:18]([C:20]1[CH:21]=[C:22]([OH:26])[CH:23]=[CH:24][CH:25]=1)=[O:19].C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>CC(C)=O>[F:13][C:14]([F:27])([F:28])[CH2:15][CH2:16][CH2:17][C:18]([C:20]1[CH:21]=[C:22]([CH:23]=[CH:24][CH:25]=1)[O:26][CH2:2][C:3]1[CH:12]=[CH:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]=1)=[O:19]

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 203942-(Chloromethyl)quinolineHCID 21280555HCID 21280555, compound

Product 1

HCID 14349144HCID 14349144, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

This material was synthesized by refluxing a mixture of 2-chloromethyl quinoline (2.6 g, 14.5 mmol), 3-(5,5,5-trifluoropentanoyl)phenol (3.7 g, 15.9 mmol), powdered potassium carbonate (6.0 g, 43.5 mmol) and a catalytic amount of potassium iodide (0.1 g) in dry acetone (50 ml) for 14 hours. After this period, the mixture was filtered, and the filtrate was concentrated. The residue was dissolved in ether, and the ethereal solution was washed with brine, dried over MgSO4, and then concentrated in vacuo. The pure desired ketone was isolated by chromatography on silica gel using 20% ethyl acetate in hexanes as eluent. The product was obtained in 62% yield (3.4 g), had a melting point 80°-82° C. and was a yellowish solid.

Workup

  1. customThis material was synthesized
  2. temperatureby refluxing
  3. waitAfter this period
  4. filtrationthe mixture was filtered
  5. concentrationthe filtrate was concentrated
  6. dissolutionThe residue was dissolved in ether
  7. washthe ethereal solution was washed with brine
  8. dry with materialdried over MgSO4
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-716bbcef413e48948e4a21a34f8139e1
Source dataset
uspto-grants-1988_12
Patent number
US04794188

Reaction notes

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