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2-(Trimethylsiloxy)-1,3-butadiene → 10a-(4-Chloro-benzenesulfonyl)-1,4-difluoro-6a,9,10,10a-tetrahydro-6H,7H-benzo[c]chromen-8-one

HRID 564331
ノート
印刷プレビュー

反応式

HRID 564331 の反応式
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([C:11]2[C:20]3[C:15](=[C:16]([F:22])[CH:17]=[CH:18][C:19]=3[F:21])[O:14][CH2:13][CH:12]=2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.C[Si](C)(C)[O:25][C:26](=[CH2:29])[CH:27]=[CH2:28]>FC(F)(F)C1C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([S:8]([C:11]23[CH2:28][CH2:27][C:26](=[O:25])[CH2:29][CH:12]2[CH2:13][O:14][C:15]2[C:20]3=[C:19]([F:21])[CH:18]=[CH:17][C:16]=2[F:22])(=[O:9])=[O:10])=[CH:6][CH:7]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

4

反応物 2

HCID 5546572-(Trimethylsiloxy)-1,3-butadieneHCID 582522424-((4-Chlorophenyl)sulfonyl)-5,8-difluoro-2H-chromene

生成物 1

HCID 4688486510a-(4-Chloro-benzenesulfonyl)-1,4-difluoro-6a,9,10,10a-tetrahydro-6H,7H-benzo[c]chromen-8-one収率 52.3%

試薬・触媒・溶媒 1

HCID 7368(Trifluoromethyl)benzene溶媒

反応条件

温度
150 °C

実験手順

A mixture of 10.8 g (31.5 mmol) of the vinylsulphone product of step 3 of Example 17 and 24 g (165 mmol) of the 3-trimethylsiloxy-1,3-butadiene in 100 mL of trifluorotoluene in a sealed tube was heated at 150° C. for 15 h. It was concentrated, the residue was dissolved in 50 mL of THF. To this solution was added 3 mL of 1N HCl, the mixture was stirred at room temperature for 30 min. It was diluted with 300 mL of methylene chloride, washed with 50 mL of brine, and concentrated. The residue was recrystallized from ethyl acetate to give 6.8 g of the ketone. Chromatography of the mother liquid gave additional 3.4 g of the ketone.

後処理

  1. concentrationIt was concentrated
  2. dissolutionthe residue was dissolved in 50 mL of THF
  3. additionTo this solution was added 3 mL of 1N HCl
  4. additionIt was diluted with 300 mL of methylene chloride
  5. washwashed with 50 mL of brine
  6. concentrationconcentrated
  7. customThe residue was recrystallized from ethyl acetate

出典と根拠

ORDレコード
ord-ddacec5f922a4f22a7d05545b9e26c02
出典データセット
uspto-grants-2011_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08067621B2

反応ノート

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