tert-Butyldimethylsilyl chloride → 3-[(2-{[tert-Butyl(dimethyl)silyl]oxy}ethyl)sulfonyl]nitrobenzene

HRID 1398084Notes

Reaction equation

HRID 1398084 reaction equation
[OH:1][CH2:2][CH2:3][S:4]([C:7]1[CH:8]=[C:9]([N+:13]([O-:15])=[O:14])[CH:10]=[CH:11][CH:12]=1)(=[O:6])=[O:5].[Si:16](Cl)([C:19]([CH3:22])([CH3:21])[CH3:20])([CH3:18])[CH3:17]>ClCCl.CN(C)C1C=CN=CC=1>[Si:16]([O:1][CH2:2][CH2:3][S:4]([C:7]1[CH:8]=[C:9]([N+:13]([O-:15])=[O:14])[CH:10]=[CH:11][CH:12]=1)(=[O:6])=[O:5])([C:19]([CH3:22])([CH3:21])[CH3:20])([CH3:18])[CH3:17]

Participants

5

Reactant 2

HCID 28928tert-Butyldimethylsilyl chlorideHCID 170561Ethanol, 2-[(3-nitrophenyl)sulfonyl]-

Product 1

HCID 576979503-[(2-{[tert-Butyl(dimethyl)silyl]oxy}ethyl)sulfonyl]nitrobenzeneYield 89%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 955 mg (4.13 mmol) of 3-[(2-hydroxyethyl)sulfonyl]-nitrobenzene in 30 mL of dichloromethane were added 747 mg (4.96 mmol) of tert-butyldimethylsilyl chloride and 10 mg of 4-dimethylaminopyridine, and the mixture was stirred for over night at room temperature. Then, the reaction mixture was diluted with dichloromethane and the organic layer was washed with water and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure and the residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=4/1 to 2/1) to give 1.27 g (89%) of the title compound.

Workup

  1. washthe organic layer was washed with water
  2. dry with materialdried over anhydrous sodium sulfate
  3. customThe solvent was removed under reduced pressure
  4. customthe residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=4/1 to 2/1)

Sources & evidence

ORD record
ord-fc6b654072c24befa9d3249fb59e574c
Source dataset
uspto-grants-2014_12
Patent number
US08901315B2

Reaction notes

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