Sodium, 2,4-cyclopentadien-1-yl- → 6-Benzyl-6-(p-chlorophenyl)fulvene

HRID 630581

Reaktionsgleichung

Reaktionsgleichung von HRID 630581
[Cl-].[Mg+2].[Cl-].[CH-:4]1[CH:8]=[CH:7][CH:6]=[CH:5]1.[Na+].[CH2:10]([C:17]([C:19]1[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][CH:20]=1)=O)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>C1COCC1>[CH2:10]([C:17]([C:19]1[CH:20]=[CH:21][C:22]([Cl:25])=[CH:23][CH:24]=1)=[C:4]1[CH:8]=[CH:7][CH:6]=[CH:5]1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Komponenten

5

Edukt 3

HCID 78681Sodium, 2,4-cyclopentadien-1-yl-HCID 2338404'-Chloro-2-phenylacetophenoneHCID 5360315Magnesium Chloride

Produkt 1

HCID 1178308126-Benzyl-6-(p-chlorophenyl)fulvene

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel3×

Versuchsvorschrift

Under a nitrogen atmosphere, 2.45 g (25.7 mmol) of anhydrous magnesium chloride and 20 mL of dry THF were put into a 100-mL Schlenk flask and then stirred. To this mixed solution, 10.6 mL (21.2 mmol) of a solution of sodium cyclopentadienide having a concentration of 2.0 mol/L in THF was added. Then, the product was heated and refluxed for an hour, the obtained pink slurry was cooled in an ice bath, and a solution in which 3.5 g (17.8 mmol) of benzyl(p-chlorophenyl)ketone had been dissolved in 15 mL of dry THF was subsequently added thereto. Then, the product was stirred at room temperature for 18 hours, and the obtained orange solution was quenched with dilute aqueous hydrochloric acid. Then, 30 mL of diethyl ether was added thereto, the soluble part in diethyl ether was extracted, and the organic phase was neutralized and washed with an aqueous solution of saturated sodium hydrogen carbonate, water, and a saturated salt solution and then dehydrated with anhydrous magnesium sulfate. The solvent was distilled off, the residue was subsequently purified by silica gel column chromatography to obtain an objective that was a reddish orange solid (amount: 2.7 g), and the objective was directly used in the subsequent process.

Aufarbeitung

  1. temperatureThen, the product was heated
  2. temperaturerefluxed for an hour
  3. temperaturethe obtained pink slurry was cooled in an ice bath
  4. additionwas subsequently added
  5. stirringThen, the product was stirred at room temperature for 18 hours
  6. customthe obtained orange solution was quenched with dilute aqueous hydrochloric acid
  7. additionThen, 30 mL of diethyl ether was added
  8. extractionthe soluble part in diethyl ether was extracted
  9. washwashed with an aqueous solution of saturated sodium hydrogen carbonate, water
  10. distillationThe solvent was distilled off
  11. customthe residue was subsequently purified by silica gel column chromatography
  12. customto obtain an objective that

Quellen und Nachweise

ORD-Eintrag
ord-e0fc3f48114948a3a2869d8e3611cc6f
Quelldatensatz
uspto-grants-2016_04
Patentnummer
US09315602B2

Verknüpfte Notizen

Wird geladen…