Hydrochloric Acid → (E)-3-(4-chlorophenyl)-6-(2-naphthyl)-5-hexen-2-one

HRID 263676

Reaktionsgleichung

Reaktionsgleichung von HRID 263676
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9](=[O:11])[CH3:10])=[CH:4][CH:3]=1.[H-].[Na+].[CH:14]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH:17]=[CH:16][C:15]=1/[CH:24]=[CH:25]/[CH2:26]Br.Cl>CN(C)C=O.C1C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]([CH2:26]/[CH:25]=[CH:24]/[C:15]2[CH:16]=[CH:17][C:18]3[C:23](=[CH:22][CH:21]=[CH:20][CH:19]=3)[CH:14]=2)[C:9](=[O:11])[CH3:10])=[CH:6][CH:7]=1

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 796991-(p-Chlorophenyl)acetoneHCID 22252145(E)-3-(2-naphthyl)-2-propenyl bromide

Produkt 1

HCID 19038600(E)-3-(4-chlorophenyl)-6-(2-naphthyl)-5-hexen-2-oneAusbeute 78 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 241BenzeneLösungsmittel2×HCID 6228DimethylformamideLösungsmittel2×

Versuchsvorschrift

2.56 g of p-chlorophenylacetone was dissolved in a mixed solution of 5 ml of dimethylformamide and 5 ml of benzene, and a dimethylformamide 8 ml/benzene 8 ml solution containing 0.62 g of 60% oily sodium hydride and 3.50 g of (E)-3-(2-naphthyl)-2-propenyl bromide, was added under cooling with ice with stirring, followed by stirring at room temperature for 2 hours. The reaction solution was acidified by an addition of 1N hydrochloric acid and extracted by an addition of water and ethyl ether. Then, the organic layer was washed with a saturated sodium chloride aqueous solution and then dried over anhydrous magnesium sulfate. The drying agent was filtered off, and then, the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=5/1) to obtain 3.70 g of the above-identified compound.

Aufarbeitung

  1. additionwas added
  2. temperatureunder cooling with ice
  3. stirringby stirring at room temperature for 2 hours
  4. extractionextracted by an addition of water and ethyl ether
  5. washThen, the organic layer was washed with a saturated sodium chloride aqueous solution
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationThe drying agent was filtered off
  8. distillationthe solvent was distilled off under reduced pressure
  9. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=5/1)

Quellen und Nachweise

ORD-Eintrag
ord-397ef8e10d194d67a54872cfd2b6b3e6
Quelldatensatz
uspto-grants-1997_07
Patentnummer
US05643958

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