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

HRID 1246545노트

반응식

HRID 1246545 반응식
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]

참가 물질

8

반응물 4

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

생성물 1

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

시약·촉매·용매 3

HCID 962Water용매HCID 8028Tetrahydrofuran용매HCID 8058Hexane용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-7932c995cf9a41b9b52e44f59945cd43
출처 데이터셋
uspto-grants-2006_10
특허 번호
US07125901B2

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