Water → {3-[(4-Bromophenyl)sulfonyl]propoxy}(tert-butyl)dimethylsilane

HRID 70584ノート

反応式

HRID 70584 の反応式
[C:1]([Si:5]([CH3:8])([CH3:7])Cl)([CH3:4])([CH3:3])[CH3:2].C(N(C(C)C)CC)(C)C.[Br:18][C:19]1[CH:24]=[CH:23][C:22]([S:25]([CH2:28][CH2:29][CH2:30][OH:31])(=[O:27])=[O:26])=[CH:21][CH:20]=1.O>CN(C)C=O>[Br:18][C:19]1[CH:20]=[CH:21][C:22]([S:25]([CH2:28][CH2:29][CH2:30][O:31][Si:5]([C:1]([CH3:4])([CH3:3])[CH3:2])([CH3:8])[CH3:7])(=[O:26])=[O:27])=[CH:23][CH:24]=1

参加物

6

反応物 4

HCID 962WaterHCID 28928tert-Butyldimethylsilyl chloride3 回HCID 81531Diisopropylethylamine3 回HCID 28355626HCID 28355626、化合物

生成物 1

HCID 58452894{3-[(4-Bromophenyl)sulfonyl]propoxy}(tert-butyl)dimethylsilane収率 65.2%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

tert-Butyldimethylchlorosilane (508 mg) and diisopropylethylamine (587 μL) were added to a solution of 3-(4-bromophenylsulfonyl)propan-1-ol (784 mg) in N,N-dimethylformamide (4 mL), and the mixture was stirred at room temperature for 2.5 hours. tert-Butyldimethylchlorosilane (127 mg) and diisopropylethylamine (147 μL) were added to the reaction solution, and the mixture was stirred at room temperature for further two hours. tert-Butyldimethylchlorosilane (254 mg) and diisopropylethylamine (1.17 mL) were added to the reaction solution, and the mixture was stirred at room temperature for further 30 minutes. Water was added to the reaction solution, followed by extraction with chloroform. The organic layer was dried over anhydrous magnesium sulfate and filtered. The solvent was then evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=50:1→33:1→19:1→9:1) to give the title compound as a white solid (720 mg, 65%).

後処理

  1. stirringthe mixture was stirred at room temperature for further two hours
  2. stirringthe mixture was stirred at room temperature for further 30 minutes
  3. extractionfollowed by extraction with chloroform
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. customThe solvent was then evaporated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=50:1→33:1→19:1→9:1)

出典と根拠

ORDレコード
ord-e5626cb46df84677afeec3aadaf04f87
出典データセット
uspto-grants-2014_09
特許番号
US08822503B2

反応ノート

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