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

HRID 857842Notes

Reaction equation

HRID 857842 reaction equation
[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

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent4×

Procedure

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).

Workup

  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%)

Sources & evidence

ORD record
ord-27c9ed4ae2bd46f59e3e8955c5c22358
Source dataset
uspto-grants-2006_12
Patent number
US07148173B2

Reaction notes

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