Tetrahydrofuran → HCID 178504158, compound

HRID 1370751Notes

Reaction equation

HRID 1370751 reaction equation
[Cl-:1].[Cl-].[Cl-].[Cl-].[Zr+4:5].[CH2:6]1[CH2:10]O[CH2:8][CH2:7]1.[CH3:11][Si:12]1([CH:16]2[C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[CH:18]=[CH:17]2)[CH2:15][CH2:14][CH2:13]1.[Li]>ClCCl>[Cl-:1].[Cl-:1].[CH3:11][Si:12]1([C:7]2[CH:8]([Zr+2:5][CH:24]3[C:19]4[C:18](=[CH:23][CH:22]=[CH:21][CH:20]=4)[CH:17]=[C:16]3[Si:12]3([CH3:11])[CH2:13][CH2:14][CH2:15]3)[C:18]3[C:10]([CH:6]=2)=[CH:23][CH:24]=[CH:16][CH:17]=3)[CH2:15][CH2:14][CH2:13]1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 9856075Zirconium chloride (ZrCl4), (T-4)-HCID 70012514HCID 70012514, compound

Product 1

HCID 178504158HCID 178504158, compoundYield 86.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Under nitrogen atmosphere, 4.46 g (21.65 mmol) of lithium 1-(1-methyl-1-silacyclobutyl)indene and 4.08 g (10.81 mmol) of ZrCl4(THF)2, which was obtained by reacting ZrCl4 with THF, was placed in each flask respectively. 50 mL of dichloromethane was added to each flask with stirring for about 30 minutes to form suspension. The suspension of ZrCl4(THF)2 in the second flask was slowly added into the suspension of lithium 1-(1-methyl-1-silacyclobutyl)indene in the first flask, and then the remained solid in the second flask was washed with 10 mL of dichloromethane and added into the first flask. With repeating the washing and addition process for three times, the reaction mixture was stirred overnight. After completion of reaction, LiCl was filtered and removed from yellowish solution with 11G4 filter. The solvent was then evaporated from the filtrate under vacuum until solid powder is formed in the filtrate. The condensed filtrate was placed at −20° C. for about 24 hours for crystallization. The yellowish powder formed by crystallization was filtered, washed several times with hexane, and dried under vacuum overnight to obtain 5.25 g (yield: 86.6%) of pure bis((1-methyl-1-silacyclobutyl)indenyl)zirconium dichloride having the following 1H NMR (CDCl3, ppm) data: δ7.9-7.27 (m, 8H, Ar), 6.59 (d, 2H, 2-lndH), 6.35 (d, 2H, 3-lndH), 2.36-2.11 (m, 4H), 1.50-1.22 (m, 4H), 0.68 (s, 6H, 2CH3).

Workup

  1. customwas placed in each flask
  2. customto form suspension
  3. washthe remained solid in the second flask was washed with 10 mL of dichloromethane
  4. additionadded into the first flask
  5. additionaddition process for three times
  6. stirringthe reaction mixture was stirred overnight
  7. customAfter completion of reaction, LiCl
  8. filtrationwas filtered
  9. customremoved from yellowish solution with 11G4
  10. filtrationfilter
  11. customThe solvent was then evaporated from the filtrate under vacuum until solid powder
  12. customis formed in the filtrate
  13. customThe condensed filtrate was placed at −20° C. for about 24 hours for crystallization
  14. customThe yellowish powder formed by crystallization
  15. filtrationwas filtered
  16. washwashed several times with hexane
  17. customdried under vacuum overnight

Sources & evidence

ORD record
ord-c923e952ea844d71be8028f2c0c750dd
Source dataset
uspto-grants-2003_06
Patent number
US06583304B2

Reaction notes

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