Chlorotrimethylsilane → 2-Trimethylsilyl-3-methoxythiophene

HRID 6961

反応式

HRID 6961 の反応式
[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]

参加物

5

反応物 3

HCID 6397ChlorotrimethylsilaneHCID 1402493-MethoxythiopheneHCID 178418339Butyllithium

生成物 1

HCID 110086402-Trimethylsilyl-3-methoxythiophene収率 82%

試薬・触媒・溶媒 1

HCID 3283Diethyl Ether溶媒

反応条件

温度
-70 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-565e2ecce6004964ad51bb958a449fdc
出典データセット
uspto-grants-2006_08
特許番号
US07084170B2

関連ノート

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