Silacyclohexane, 1,1-dichloro- → Chloro-2,3,4,5-tetramethylcyclopentadienyl silacyclohexane

HRID 1015680Notes

Reaction equation

HRID 1015680 reaction equation
[CH3:1][C:2]1[CH2:3][C:4]([CH3:9])=[C:5]([CH3:8])[C:6]=1[CH3:7].C([Li])CCC.[Cl:15][Si:16]1(Cl)[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1>O1CCCC1>[Cl:15][Si:16]1([CH:3]2[C:2]([CH3:1])=[C:6]([CH3:7])[C:5]([CH3:8])=[C:4]2[CH3:9])[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1

Participants

5

Reactant 3

HCID 75475Silacyclohexane, 1,1-dichloro-HCID 1381631,2,3,4-TetramethylcyclopentadieneHCID 178418339Butyllithium

Product 1

HCID 131729073Chloro-2,3,4,5-tetramethylcyclopentadienyl silacyclohexaneYield 91.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Into a flask containing 100 ml of tetrahydrofuran, 2,3,4,5-tetramethylcyclopenta-2,4-diene (3.67 g, 30 mmol) was added, and then n-butyl lithium (12 ml) was added in droplets thereto at 0° C. The reaction temperature was gradually increased to room temperature, and the reaction mixture was allowed to react for 8 hours. The temperature of the reaction solution was decreased to −78° C., after which the reaction solution was added with dichlorosilacyclohexane (5.07 g, 30 mmol) and then allowed to react for 12 hours. After the reaction, volatile material was removed, the resultant reaction product was extracted with 100 ml of hexane, and more volatile material was removed, thus obtaining 7.01 g of chloro-2,3,4,5-tetramethylcyclopentadienyl silacyclohexane as light yellow oil. Subsequently, the chloro-2,3,4,5-tetramethylcyclopentadienyl silacyclohexane thus obtained was dissolved in 100 ml of tetrahydrofuran, without additional purification, and 2.18 g of lithium tert-butylamide was added in droplets thereto at 0° C., after which the reaction mixture was allowed to react at room temperature for 2 hours. After the reaction, the volatile material was removed, the resultant reaction product was extracted with 100 ml of hexane, and more volatile material was removed, thus obtaining 7.42 g of (tert-butylamido)(2,3,4,5-tetramethylcyclopenta-2,4-dienyl)silacyclohexane as light yellow oil.

Workup

  1. additionwas added
  2. customat 0° C
  3. customto react for 8 hours
  4. customwas decreased to −78° C.
  5. customto react for 12 hours
  6. customAfter the reaction, volatile material
  7. customwas removed
  8. customthe resultant reaction product
  9. extractionwas extracted with 100 ml of hexane, and more volatile material
  10. customwas removed

Sources & evidence

ORD record
ord-8c746458a41845a8bdd35833eb69e725
Source dataset
uspto-grants-2011_07
Patent number
US07985817B2

Reaction notes

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