4-(4'-Hydroxyphenyl)-2-butanone → HCID 23119605, Verbindung

HRID 458501

Reaktionsgleichung

Reaktionsgleichung von HRID 458501
[H-].[Na+].[OH:3][C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH2:11][C:12](=[O:14])[CH3:13])=[CH:6][CH:5]=1.Br[CH2:16][CH2:17][CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20]>CN(C=O)C>[O:14]=[C:12]([CH3:13])[CH2:11][CH2:10][C:7]1[CH:6]=[CH:5][C:4]([O:3][CH2:16][CH2:17][CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20])=[CH:9][CH:8]=1

Komponenten

5

Edukt 3

HCID 216484-(4'-Hydroxyphenyl)-2-butanoneHCID 24758Sodium hydrideHCID 76300Ethyl 4-bromobutyrate

Produkt 1

HCID 23119605HCID 23119605, VerbindungAusbeute 50 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel3×

Versuchsvorschrift

To a suspension of sodium hydride (60% dispersion in mineral oil) (7.3 g, 0.183 mole) in anhydrous DMF (100 ml) under nitrogen atmosphere was added drop-wise 4-(4-hydroxyphenyl)-2-butanone 2 (20.0 g, 0.122 mole) in anhydrous DMF (100 ml) and the mixture was then stirred at room temperature for one hour. To this mixture was added drop-wise ethyl 4-bromobutyrate (28.5 g, 0.146 mole) in anhydrous DMF (50 ml), and the mixture was then stirred at 60° C. overnight. The DMF was removed under reduced pressure and water (200 ml) was then added to the residue and extracted with ethyl acetate (3×200 ml). The combined organic phases were washed with brine (1×200 ml), dried over magnesium sulfate, filtered and evaporated to dryness. The residue obtained was purified by flash chromatography on silica gel using 20% ethyl acetate in hexane as eluant to give 3 as a colourless oil (16.95 g, 50%).

Aufarbeitung

  1. stirringthe mixture was then stirred at 60° C. overnight
  2. customThe DMF was removed under reduced pressure and water (200 ml)
  3. additionwas then added to the residue
  4. extractionextracted with ethyl acetate (3×200 ml)
  5. washThe combined organic phases were washed with brine (1×200 ml)
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. customevaporated to dryness
  9. customThe residue obtained
  10. customwas purified by flash chromatography on silica gel using 20% ethyl acetate in hexane as eluant

Quellen und Nachweise

ORD-Eintrag
ord-74653f9c92f24ed3840da768dae1b96e
Quelldatensatz
uspto-grants-2007_03
Patentnummer
US07192722B2

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