Hydrochloric Acid → 1-[3-(2-{[Tert-butyl(dimethyl)silyl]oxy}ethyl)phenyl]ethanone

HRID 2117958Notes

Reaction equation

HRID 2117958 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH2:8][CH2:9][O:10][Si:11]([C:14]([CH3:17])([CH3:16])[CH3:15])([CH3:13])[CH3:12])[CH:5]=[CH:6][CH:7]=1.[Li]CCCC.[CH3:23][C:24](N(C)C)=[O:25].Cl>O1CCCC1.CCCCCC.O>[Si:11]([O:10][CH2:9][CH2:8][C:4]1[CH:3]=[C:2]([C:24](=[O:25])[CH3:23])[CH:7]=[CH:6][CH:5]=1)([C:14]([CH3:17])([CH3:16])[CH3:15])([CH3:13])[CH3:12]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 31374DimethylacetamideHCID 11515183(3-Bromophenethoxy)(tert-butyl)dimethylsilaneHCID 178418339Butyllithium

Product 1

HCID 692256631-[3-(2-{[Tert-butyl(dimethyl)silyl]oxy}ethyl)phenyl]ethanone

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Procedure

To a solution of 1.6 g of [2-(3-bromophenyl)ethoxy](tert-butyl)dimethylsilane in tetrahydrofuran (20 ml) was added n-BuLi in hexane (1.57M, 3.88 ml) at −70° C., then the reaction mixture was stirred at same temperature for 30 min. To the solution was added dimethylacetamide (1.42 ml) drop wise at the same temperature. The mixture was stirred for another 1 hour. To the reaction mixture were added water and 8 ml of 1N HCl under ice-cooling. The mixture was stirred for 1 hour, then extracted with ethyl acetate. The organic layer was washed with brine, dried over magnesium sulfate and concentrated in vacuo. The residue was purified by silica gel column chromatography with n-hexane and ethyl acetate (20/1-10/1) as an eluent to give 1-[3-(2-{[tert-butyl(dimethyl)silyl]oxy}ethyl)phenyl]ethanone (350 mg) as colorless oil.

Workup

  1. stirringThe mixture was stirred for another 1 hour
  2. temperaturecooling
  3. stirringThe mixture was stirred for 1 hour
  4. extractionextracted with ethyl acetate
  5. washThe organic layer was washed with brine
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by silica gel column chromatography with n-hexane and ethyl acetate (20/1-10/1) as an eluent

Sources & evidence

ORD record
ord-cd8591cf000846bf9cc580243900b090
Source dataset
uspto-grants-2008_10
Patent number
US07442715B2

Reaction notes

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