(Trimethylsilyl)imidazole → [1-(3-Bromo-phenyl)-1-ethyl-propoxy]-trimethyl-silane

HRID 546829노트

반응식

HRID 546829 반응식
[CH3:1][Si:2]([CH3:9])([CH3:8])N1C=CN=C1.[Br:10][C:11]1[CH:12]=[C:13]([C:17]([OH:22])([CH2:20][CH3:21])[CH2:18][CH3:19])[CH:14]=[CH:15][CH:16]=1>O1CCCC1>[Br:10][C:11]1[CH:12]=[C:13]([C:17]([CH2:18][CH3:19])([O:22][Si:2]([CH3:1])([CH3:8])[CH3:9])[CH2:20][CH3:21])[CH:14]=[CH:15][CH:16]=1

참가 물질

4

반응물 2

HCID 28925(Trimethylsilyl)imidazoleHCID 574434823-(3-Bromophenyl)pentan-3-ol

생성물 1

HCID 57709150[1-(3-Bromo-phenyl)-1-ethyl-propoxy]-trimethyl-silane수율 59%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

N-trimethylsilylimidazole (8.2 mL, 55.81 mol) was added to a solution of the crude 3-(3-bromo-phenyl)-pentan-3-ol in tetrahydrofuran (100 mL) in a nitrogen atmosphere at room temperature, and the mixture was stirred overnight. The reaction mixture was poured into distilled water, followed by extraction with dichloromethane. The extract was washed with brine, dried over anhydrous magnesium sulfate and filtered, and the solvent was distilled off under reduced pressure. The residue was subjected to silica gel chromatography (n-hexane:ethyl acetate=40:1) to give the title compound as a colorless oil (8.7 g, 59% in two steps).

후처리

  1. additionThe reaction mixture was poured
  2. distillationinto distilled water
  3. extractionfollowed by extraction with dichloromethane
  4. washThe extract was washed with brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. distillationthe solvent was distilled off under reduced pressure

출처 및 근거

ORD 기록
ord-544cf9b858404d80848f9f6f4473e1c7
출처 데이터셋
uspto-grants-2011_05
특허 번호
US07935688B2

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