2-Phenylacetophenone → 6-Benzyl-6-phenylfulvene

HRID 630580

反応式

HRID 630580 の反応式
[Cl-].[Mg+2].[Cl-].[CH-:4]1[CH:8]=[CH:7][CH:6]=[CH:5]1.[Na+].[C:10]1([C:16]([CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=O)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>C1COCC1>[CH2:18]([C:16]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[C:4]1[CH:8]=[CH:7][CH:6]=[CH:5]1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

参加物

5

反応物 3

HCID 99482-PhenylacetophenoneHCID 78681Sodium, 2,4-cyclopentadien-1-yl-HCID 5360315Magnesium Chloride

生成物 1

HCID 1317354076-Benzyl-6-phenylfulvene収率 62%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒3 回

実験手順

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 2.0-M sodium cyclopentadienide in THF was added. Then, the product was heated for an hour under reflux, the obtained pink slurry was cooled in an ice bath, and a solution in which 3.5 g (17.8 mmol) of benzyl phenyl 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 layer 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, and then the residue was purified by silica gel column chromatography to obtain an objective that was a reddish orange solid (amount: 2.7 g and yield: 62%).

後処理

  1. temperatureThen, the product was heated for an hour
  2. temperatureunder reflux
  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 purified by silica gel column chromatography
  12. customto obtain an objective that

出典と根拠

ORDレコード
ord-745d0957f6ac48bfab6ddad895db4308
出典データセット
uspto-grants-2016_04
特許番号
US09315602B2

関連ノート

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