Allyl bromide → 4-Trifluoromethyl-8-propyl-7-hydroxycoumarin

HRID 342778

Reaktionsgleichung

Reaktionsgleichung von HRID 342778
[F:1][C:2]([F:16])([F:15])[C:3]1[C:12]2[C:7](=[CH:8][C:9]([OH:13])=[CH:10][CH:11]=2)[O:6][C:5](=[O:14])[CH:4]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:24][CH:25]=[CH2:26]>CN(C=O)C.C(OCC)(=O)C.CO.[Pd]>[F:16][C:2]([F:1])([F:15])[C:3]1[C:12]2[C:7](=[C:8]([CH2:24][CH2:25][CH3:26])[C:9]([OH:13])=[CH:10][CH:11]=2)[O:6][C:5](=[O:14])[CH:4]=1

Komponenten

8

Edukt 3

HCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 53756677-Hydroxy-4-trifluoromethylcoumarin

Produkt 1

HCID 537014304-Trifluoromethyl-8-propyl-7-hydroxycoumarin

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 23938PalladiumKatalysatorHCID 887MethanolLösungsmittelHCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of 4-trifluoromethyl-7-hydroxycoumarin (5.0 grams, 22.0 mmol) and potassium carbonate(3.6 grams, 26.0 mmol) in DMF (20.0 mL) at 40° C., was added 3-bromoprop-1-ene (2.0 mL, 23.0 mmol). This mixture was stirred 18 hours and then diluted with ethyl acetate. The organic phase was washed with 1M hydrochloric acid solution and brine. The organic was then dried over sodium sulfate and the solvent removed to give a tan solid. This was filtered through a pad of silica gel using 20% ethylacetate in hexane. This material was then dissolved in 1,2-dichlorobenzene (150 mL) and refluxed for 18 hours. The solvent was removed in vacuo to give a tan solid. This material was dissolved in methanol (150 mL) with 10% palladium on carbon (300.0 mg) under a hydrogen atmosphere (1 Atm) for 2 hours. The mixture was then filtered through a celite pad and the solvent removed in vacuo to give tan solid. This was chromatographed on silica gel using 20% ethyl acetate in hexane to give the titled compound.

Aufarbeitung

  1. washThe organic phase was washed with 1M hydrochloric acid solution and brine
  2. dry with materialThe organic was then dried over sodium sulfate
  3. customthe solvent removed
  4. customto give a tan solid
  5. filtrationThis was filtered through a pad of silica gel using 20% ethylacetate in hexane
  6. dissolutionThis material was then dissolved in 1,2-dichlorobenzene (150 mL)
  7. temperaturerefluxed for 18 hours
  8. customThe solvent was removed in vacuo
  9. customto give a tan solid
  10. filtrationThe mixture was then filtered through a celite pad
  11. customthe solvent removed in vacuo
  12. customto give tan solid
  13. customThis was chromatographed on silica gel using 20% ethyl acetate in hexane

Quellen und Nachweise

ORD-Eintrag
ord-f9f181e5f89a40b18ad706533f460adb
Quelldatensatz
uspto-grants-1999_01
Patentnummer
US05859051

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