Silane, dimethyldi(2,4-cyclopentadien-1-yl)- → (2-Trimethylsiloxyethylcyclopentadienyl) dimethyl cyclopentadienyl silane

HRID 857843Notes

Reaction equation

HRID 857843 reaction equation
[CH:1]1([Si:6]([CH:9]2[CH:13]=[CH:12][CH:11]=[CH:10]2)([CH3:8])[CH3:7])[CH:5]=[CH:4][CH:3]=[CH:2]1.Br[CH2:15][CH2:16][O:17][Si:18]([CH3:21])([CH3:20])[CH3:19]>C1COCC1>[CH3:19][Si:18]([CH3:21])([CH3:20])[O:17][CH2:16][CH2:15][C:9]1([Si:6]([CH3:7])([CH3:8])[CH:1]2[CH:2]=[CH:3][CH:4]=[CH:5]2)[CH:10]=[CH:11][CH:12]=[CH:13]1

Participants

4

Reactant 2

HCID 579493Silane, dimethyldi(2,4-cyclopentadien-1-yl)-HCID 587231(2-Bromoethoxy)trimethylsilane

Product 1

HCID 131726162(2-Trimethylsiloxyethylcyclopentadienyl) dimethyl cyclopentadienyl silaneYield 52%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent4×

Procedure

A solution of 11.5 g (61 mmol) of biscyclopentadienyidimethylsilane in THF was added to a suspension of 1.3 g (55 mmol) of HK in THF at −78° C. A purple solution was immediately 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 10.8 g (55 mmol) of 2-bromo-1-trimethylsiloxyethane in THF was added at room temperature. A pink suspension was immediately formed. The mixture was stirred for 12 h, and then the solvents were removed, the residue was treated with hexane and the supernatant solution was filtered. The removal of the hexane led to a reddish oil. This oil was distilled in order to obtain a yellow oil, which was characterized as a mixture of position isomers of (2-trimethylsiloxyethylcyclopentadienyl) dimethyl cyclopentadienyl silane (Tb: 135–140° C.; 1 mm Hg), (8.7 g, 28.6 mmol, yield: 52%). 1H-RMN(CDCl3): 6.82–6.40 (m, 7H); 3.82 (m, 2H); 3.10 (m, 2H); 2.73 (m, 2H); 0.20 (s, 15 H).

Workup

  1. customA purple solution was immediately formed
  2. customThen, the volatiles were removed
  3. washthe residue was washed with hexane
  4. customto give a pink solid
  5. customA pink suspension was immediately formed
  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 oil, which

Sources & evidence

ORD record
ord-1243a0778270483a8db9ea9a1e0b301c
Source dataset
uspto-grants-2006_12
Patent number
US07148173B2

Reaction notes

Loading…