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Tetrahydrofuran → HCID 18424484、化合物

HRID 1282470
ノート
印刷プレビュー

反応式

HRID 1282470 の反応式
[Cl-].[Ce+3].[Cl-].[Cl-].[CH2:5]1COC[CH2:6]1.C([Mg]Cl)C.[F:14][C:15]1[CH:29]=[CH:28][C:18]([C:19]([C:21]2[CH:26]=[CH:25][C:24]([F:27])=[CH:23][CH:22]=2)=[O:20])=[CH:17][CH:16]=1>C(O)(=O)C>[F:14][C:15]1[CH:29]=[CH:28][C:18]([C:19]([C:21]2[CH:26]=[CH:25][C:24]([F:27])=[CH:23][CH:22]=2)([OH:20])[CH2:5][CH3:6])=[CH:17][CH:16]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 8028Tetrahydrofuran2 回HCID 95824,4'-DifluorobenzophenoneHCID 24636Cerium(III) chlorideHCID 178461633HCID 178461633、化合物

生成物 1

HCID 18424484HCID 18424484、化合物収率 78%

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒

実験手順

Into a reactor were introduced 10.0 g (40.6 mmol) of cerium chloride and 80 mL of THF under a nitrogen atmosphere. This mixture was stirred at room temperature for 20 hours and then cooled to 0° C. Thereto was added dropwise 25.1 mL (24.3 mmol; 0.97 M THF solution) of ethylmagnesium chloride over 30 minutes. Subsequently, a solution prepared by mixing 3.54 g (16.2 mmol) of 4,4′-difluorobenzophenone with 20 mL of THF was added dropwise thereto over 40 minutes, and this mixture was stirred for 1 hour. To the resultant reaction mixture was added 10% aqueous acetic acid solution. Thereafter, the mixture was extracted with ethyl acetate, and the resultant organic layer was washed with saturated aqueous sodium hydrogen carbonate solution and saturated aqueous sodium chloride solution, subsequently dried with anhydrous magnesium sulfate, and then concentrated under reduced pressure. The concentrate was purified by column chromatography to obtain 3.12 g (78%) of the target compound as a light-yellow oily substance.

後処理

  1. temperaturecooled to 0° C
  2. customSubsequently, a solution prepared
  3. additionwas added dropwise
  4. waitover 40 minutes
  5. stirringthis mixture was stirred for 1 hour
  6. customTo the resultant reaction mixture
  7. extractionThereafter, the mixture was extracted with ethyl acetate
  8. washthe resultant organic layer was washed with saturated aqueous sodium hydrogen carbonate solution and saturated aqueous sodium chloride solution
  9. dry with materialsubsequently dried with anhydrous magnesium sulfate
  10. concentrationconcentrated under reduced pressure
  11. customThe concentrate was purified by column chromatography

出典と根拠

ORDレコード
ord-93e2bd2b9b1a43b1acf030c7ad47e4c8
出典データセット
uspto-grants-2002_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06455720B1

反応ノート

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