Hydrochloric Acid → Tert-butyl(dimethyl)[2-(4-methylphenyl)ethoxy]silane

HRID 1920140Notes

Reaction equation

HRID 1920140 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][OH:10])=[CH:4][CH:3]=1.N1C=CN=[CH:12]1.[Si:16](Cl)([C:19]([CH3:22])([CH3:21])[CH3:20])([CH3:18])[CH3:17].Cl>CN(C)C=O>[C:19]([Si:16]([CH3:18])([CH3:17])[O:10][CH2:9][CH2:8][C:5]1[CH:6]=[CH:7][C:2]([CH3:12])=[CH:3][CH:4]=1)([CH3:22])([CH3:21])[CH3:20]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 728512-(4-Bromophenyl)ethanol

Product 1

HCID 23548147Tert-butyl(dimethyl)[2-(4-methylphenyl)ethoxy]silaneYield 120.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To N,N-dimethylformamide (6 mL) solution of 2-(4-bromophenyl)ethanol (552 mg), imidazole (248 mg) and tert-butyldimethylsilyl chloride (453 mg) were added. The reaction solution was stirred at room temperature for 3 hours. To the reaction solution, 1N-hydrochloric acid (10 mL) was added. The aqueous layer was extracted twice with ethyl acetate. The combined organic layer was washed with water and saturated brine and then dried over anhydrous magnesium sulfate. After removing the anhydrous magnesium sulfate by filtration, the filtrate was concentrated under reduced pressure. The residue was purified by silica gel chromatography (n-hexane:ethyl acetate=1:0→97:3) to obtain the title compound (829 mg) having the following physical properties.

Workup

  1. extractionThe aqueous layer was extracted twice with ethyl acetate
  2. washThe combined organic layer was washed with water and saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customAfter removing the anhydrous magnesium sulfate
  5. filtrationby filtration
  6. concentrationthe filtrate was concentrated under reduced pressure
  7. customThe residue was purified by silica gel chromatography (n-hexane:ethyl acetate=1:0→97:3)

Sources & evidence

ORD record
ord-1a810d82670a4598b0a180734c21063e
Source dataset
uspto-grants-2012_05
Patent number
US08168783B2

Reaction notes

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