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

HRID 630581

반응식

HRID 630581 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매3회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-e0fc3f48114948a3a2869d8e3611cc6f
출처 데이터셋
uspto-grants-2016_04
특허 번호
US09315602B2

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