18-Crown-6 → HCID 13579269, compound

HRID 1589080Notes

Reaction equation

HRID 1589080 reaction equation
Br[CH:2]1[C:6](=[O:7])[C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([C:14]([F:17])([F:16])[F:15])[CH:9]=2)=[C:4]([N:18]([CH3:20])[CH3:19])[O:3]1.C1OCCOCCOCCOCCOCCOC1.[F-:39].[K+]>C(#N)C>[F:39][CH:2]1[C:6](=[O:7])[C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([C:14]([F:17])([F:16])[F:15])[CH:9]=2)=[C:4]([N:18]([CH3:20])[CH3:19])[O:3]1

Participants

5

Reactant 3

HCID 2855718-Crown-6HCID 522689Potassium FluorideHCID 13579267HCID 13579267, compound

Product 1

HCID 13579269HCID 13579269, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

In this example, a mixture containing 3 g of 2-bromo-3-oxo-4-(3-trifluoromethylphenyl)-5-dimethylamino-2,3-dihydrofuran, 0.26 of 18-Crown-6 ether and 1.11 g of potassium fluoride in 20 ml of acetonitrile was stirred at room temperature for about 30 minutes and then refluxed overnight (about 16 hours). The mixture was then cooled, filtered, and then concentrated by evaporation. The residue was chromatographed eluting with 3 vol. % tetrahydrofuran:97% chloroform affording the title compound.

Workup

  1. temperaturerefluxed overnight (about 16 hours)
  2. temperatureThe mixture was then cooled
  3. filtrationfiltered
  4. concentrationconcentrated by evaporation
  5. customThe residue was chromatographed
  6. washeluting with 3 vol. % tetrahydrofuran

Sources & evidence

ORD record
ord-ca6b80261aa64ce98d511556b08df438
Source dataset
uspto-grants-1986_02
Patent number
US04568375

Reaction notes

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