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(2-Bromoethoxy)trimethylsilane → (2-Trimethylsiloxyethylcyclopentadienyl) indenyl dimethyl silane

HRID 857842
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인쇄 미리보기

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HRID 857842 반응식
[CH:1]1([Si:6]([CH:9]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[CH:11]=[CH:10]2)([CH3:8])[CH3:7])[CH:5]=[CH:4][CH:3]=[CH:2]1.Br[CH2:19][CH2:20][O:21][Si:22]([CH3:25])([CH3:24])[CH3:23].C[Si](C)(C)OCCC1C([Si](C2C=CC=C2)(C)C)C2C(C=1)=CC=CC=2>C1COCC1>[CH3:23][Si:22]([CH3:25])([CH3:24])[O:21][CH2:20][CH2:19][C:1]1([Si:6]([CH:9]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[CH:11]=[CH:10]2)([CH3:8])[CH3:7])[CH:5]=[CH:4][CH:3]=[CH:2]1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 587231(2-Bromoethoxy)trimethylsilaneHCID 12974858CyclopentadienylindenyldimethylsilaneHCID 131726161(2-Trimethylsiloxyethylindenyl) cyclopentadienyl dimethyl silane

생성물 1

HCID 131726160(2-Trimethylsiloxyethylcyclopentadienyl) indenyl dimethyl silane수율 42%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran
용매
4회

실험 절차

To a suspension of 0.63 g (26.3 mmol) of HNa in THF at −78° C., a solution of 6.3 g (26.3 mmol) of cyclopentadienylindenyldimethylsilane in THF was added. Immediately a purple solution was formed. Then, the volatiles were removed and the residue was washed with hexane to give a pink solid. The solid was solved again in THF and a solution of 5.2 g (26.3 mmol) of 2-bromo-1-trimethylsiloxyethane in THF was added at room temperature. A white suspension was formed immediately. The mixture was stirred for 12 h, and then the solvents were removed and the residue was treated with hexane and the supernatant solution was filtered. The removal of the hexane led to a brown oil. This oil was distilled in order to obtain a yellow-orange oil, which was characterized as a mixture of position isomers of (2-trimethylsiloxyethylindenyl) cyclopentadienyl dimethyl silane. (Tb: 170–175° C.; 1 mm Hg), (3.9 g, 11 mmol, yield: 42%). 1H-RMN(CDCl3): 7.54–7.42 (m, 2H); 7.31–7.12 (m, 2H); 6.95 (m, 1H); 6.91 (m, 1H); 6.72 (m, 1H); 6.61 (m, 1H); 6.60–6.42 (m, 3H); 3.78 (m, 2H); 3.62 (m, 1H); 3.42 (m, 2H); 2.62 (m, 2H); 0.17 (m, 15 H).

후처리

  1. customImmediately a purple solution was formed
  2. customThen, the volatiles were removed
  3. washthe residue was washed with hexane
  4. customto give a pink solid
  5. customA white suspension was formed immediately
  6. customthe solvents were removed
  7. additionthe residue was treated with hexane
  8. filtrationthe supernatant solution was filtered
  9. customThe removal of the hexane
  10. distillationThis oil was distilled in order
  11. customto obtain a yellow-orange oil, which
  12. custom(Tb: 170–175° C.; 1 mm Hg), (3.9 g, 11 mmol, yield: 42%)

출처 및 근거

ORD 기록
ord-27c9ed4ae2bd46f59e3e8955c5c22358
출처 데이터셋
uspto-grants-2006_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07148173B2

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