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

HRID 70584Notes

Reaction equation

HRID 70584 reaction equation
[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

Participants

6

Reactant 4

HCID 962WaterHCID 28928tert-Butyldimethylsilyl chloride3×HCID 81531Diisopropylethylamine3×HCID 28355626HCID 28355626, compound

Product 1

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

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

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%).

Workup

  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)

Sources & evidence

ORD record
ord-e5626cb46df84677afeec3aadaf04f87
Source dataset
uspto-grants-2014_09
Patent number
US08822503B2

Reaction notes

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