Chlorotrimethylsilane → 2-(3-Trimethylsilylcyclopentadienyl)-2-(3,6-di-tert-butylfluorenyl)propane

HRID 271007Notes

Reaction equation

HRID 271007 reaction equation
[CH:1]1([C:6]([C:9]2[C:21]3[CH2:20][C:19]4[C:14](=[CH:15][C:16]([C:22]([CH3:25])([CH3:24])[CH3:23])=[CH:17][CH:18]=4)[C:13]=3[CH:12]=[C:11]([C:26]([CH3:29])([CH3:28])[CH3:27])[CH:10]=2)([CH3:8])[CH3:7])[CH:5]=[CH:4][CH:3]=[CH:2]1.[Li]CCCC.Cl[Si:36]([CH3:39])([CH3:38])[CH3:37]>C1COCC1>[CH3:37][Si:36]([CH3:39])([CH3:38])[C:3]1[CH:4]=[CH:5][CH:1]([C:6]([C:9]2[C:21]3[CH2:20][C:19]4[C:14](=[CH:15][C:16]([C:22]([CH3:25])([CH3:24])[CH3:23])=[CH:17][CH:18]=4)[C:13]=3[CH:12]=[C:11]([C:26]([CH3:29])([CH3:28])[CH3:27])[CH:10]=2)([CH3:8])[CH3:7])[CH:2]=1

Participants

5

Reactant 3

HCID 6397ChlorotrimethylsilaneHCID 1317251292-(Cyclopentadienyl)-2-(3,6-di-tert-butylfluorenyl)propaneHCID 178418339Butyllithium

Product 1

HCID 1317271812-(3-Trimethylsilylcyclopentadienyl)-2-(3,6-di-tert-butylfluorenyl)propaneYield 84.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In a 50 ml Schlenk flask purged with nitrogen, 1.44 g (3.74 mmol, 1 eq) of 2-(cyclopentadienyl)-2-(3,6-di-tert-butylfluorenyl)propane was placed at room temperature. Then, 20 ml of dehydrated THF was added, and the mixture was stirred by a magnetic stirrer to give a solution. The solution was cooled with an ice bath (light yellowish orange solution). To the solution, 2.5 ml (1.63 mmol, 1.09 eq) of n-BuLi (hexane solution) was dropwise added. The ice bath was removed, and the solution was stirred at room temperature for 19 hours (dark red solution). The solution was cooled with an ice bath, and to the solution, 2.7 ml (21.3 mmol, 5.70 eq) of chlorotrimethylsilane was dropwise added by a syringe. The ice bath was removed, and the solution was stirred at room temperature for 3 hours. The resulting yellow solution was poured into 80 ml of a diluted hydrochloric acid solution to perform quenching. After the soluble component was extracted with 100 ml of diethyl ether, the organic phase was washed with 50 ml of a saturated saline solution. The organic phase was dried over MgSO4, then the MgSO4 was filtered off, and from the filtrate the solvent was vacuum distilled off by a rotary evaporator to obtain a light yellow solid. The solid was washed with 50 ml of methanol and vacuum dried to obtain 1.44 g a light creamy powder (yield: 84%)

Workup

  1. customwas placed at room temperature
  2. customto give a solution
  3. temperatureThe solution was cooled with an ice bath (light yellowish orange solution)
  4. customThe ice bath was removed
  5. stirringthe solution was stirred at room temperature for 19 hours (dark red solution)
  6. temperatureThe solution was cooled with an ice bath
  7. customThe ice bath was removed
  8. stirringthe solution was stirred at room temperature for 3 hours
  9. additionThe resulting yellow solution was poured into 80 ml of a diluted hydrochloric acid solution
  10. customto perform quenching
  11. extractionAfter the soluble component was extracted with 100 ml of diethyl ether
  12. washthe organic phase was washed with 50 ml of a saturated saline solution
  13. dry with materialThe organic phase was dried over MgSO4
  14. filtrationthe MgSO4 was filtered off
  15. distillationdistilled off by a rotary evaporator
  16. customto obtain a light yellow solid
  17. washThe solid was washed with 50 ml of methanol and vacuum
  18. customdried

Sources & evidence

ORD record
ord-375edcb7cca3482c8b4b6b787ba473a0
Source dataset
uspto-grants-2008_11
Patent number
US07449533B2

Reaction notes

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