Chlorotrimethylsilane → 2-Trimethylsilyl-3-methoxythiophene

HRID 6961

반응식

HRID 6961 반응식
[Li]CCCC.[CH3:6][O:7][C:8]1[CH:12]=[CH:11][S:10][CH:9]=1.Cl[Si:14]([CH3:17])([CH3:16])[CH3:15]>CCOCC>[CH3:15][Si:14]([CH3:17])([CH3:16])[C:9]1[S:10][CH:11]=[CH:12][C:8]=1[O:7][CH3:6]

참가 물질

5

반응물 3

HCID 6397ChlorotrimethylsilaneHCID 1402493-MethoxythiopheneHCID 178418339Butyllithium

생성물 1

HCID 110086402-Trimethylsilyl-3-methoxythiophene수율 82%

시약·촉매·용매 1

HCID 3283Diethyl Ether용매

반응 조건

온도
-70 °C

실험 절차

A solution of n-BuLi (19.7 mL of 1.6 M in hexanes, 31.5 mmol) is added dropwise to a solution of 3-methoxythiophene (3.0 g, 26.3 mmol) in anhydrous Et2O (20 mL) under nitrogen at −70° C. The mixture is stirred at −70° C. for 2 hr. Chlorotrimethylsilane (4.5 mL, 35.4 mmol) is added slowly to the solution. The mixture is warmed to room temperature and stirred for 3 hr. The reaction is quenched with water (50 mL) and hexanes (100 mL). The aqueous layer is extracted with hexanes (50 mL). The combined organic extracts are dried (Na2SO4), filtered and concentrated. The crude product is chromatographed on silica gel, eluting with hexanes to afford the title compound (4.0 g, 82%) as a colorless liquid.

후처리

  1. temperatureThe mixture is warmed to room temperature
  2. stirringstirred for 3 hr
  3. customThe reaction is quenched with water (50 mL) and hexanes (100 mL)
  4. extractionThe aqueous layer is extracted with hexanes (50 mL)
  5. dry with materialThe combined organic extracts are dried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe crude product is chromatographed on silica gel
  9. washeluting with hexanes

출처 및 근거

ORD 기록
ord-565e2ecce6004964ad51bb958a449fdc
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07084170B2

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