Chlorotrimethylsilane → HCID 131725140, compound

HRID 271024Notes

Reaction equation

HRID 271024 reaction equation
[CH:1]1([C:6]2([C:12]3[C:24]4[CH2:23][C:22]5[C:17](=[CH:18][C:19]([C:25]([CH3:28])([CH3:27])[CH3:26])=[CH:20][CH:21]=5)[C:16]=4[CH:15]=[C:14]([C:29]([CH3:32])([CH3:31])[CH3:30])[CH:13]=3)[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]2)[CH:5]=[CH:4][CH:3]=[CH:2]1.[Li]CCCC.Cl[Si:39]([CH3:42])([CH3:41])[CH3:40]>C1COCC1>[CH3:40][Si:39]([CH3:42])([CH3:41])[C:3]1[CH:4]=[CH:5][CH:1]([C:6]2([C:12]3[C:24]4[CH2:23][C:22]5[C:17](=[CH:18][C:19]([C:25]([CH3:26])([CH3:28])[CH3:27])=[CH:20][CH:21]=5)[C:16]=4[CH:15]=[C:14]([C:29]([CH3:32])([CH3:31])[CH3:30])[CH:13]=3)[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]2)[CH:2]=1

Participants

5

Reactant 3

HCID 6397ChlorotrimethylsilaneHCID 131725139HCID 131725139, compoundHCID 178418339Butyllithium

Product 1

HCID 131725140HCID 131725140, compoundYield 46%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In a 30 ml Schlenk flask purged with nitrogen, 0.86 g (2.02 mmol, 1 eq) of 1-(cyclopentadienyl)-1-(3,6-di-tert-butylfluorenyl)cyclohexane was placed at room temperature. Then, 12 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 (colorless transparent solution). To the solution, 1.4 ml (2.28 mmol, 1.13 eq) of n-BuLi (hexane solution) was dropwise added. Then, the ice bath was removed, and the solution was stirred at room temperature for 19 hours. The solution was cooled with an ice bath, and to the solution, 1.6 ml (12.6 mmol, 6.24 eq) of chlorotrimethylsilane was dropwise added by a syringe. The ice bath was removed, and the solution was stirred at room temperature for 4 hours. The resulting yellow solution was poured into 50 ml of a diluted hydrochloric acid solution-to perform quenching. After the soluble component was extracted with 70 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 yellow amorphous product. The amorphous product was purified by silica gel column chromatography (developing solution: hexane) to obtain 0.46 g a white amorphous product (yield: 46%).

Workup

  1. customwas placed at room temperature
  2. customto give a solution
  3. temperatureThe solution was cooled with an ice bath (colorless transparent solution)
  4. customThen, the ice bath was removed
  5. stirringthe solution was stirred at room temperature for 19 hours
  6. temperatureThe solution was cooled with an ice bath
  7. customThe ice bath was removed
  8. stirringthe solution was stirred at room temperature for 4 hours
  9. additionThe resulting yellow solution was poured into 50 ml of a diluted hydrochloric acid solution-to
  10. customperform quenching
  11. extractionAfter the soluble component was extracted with 70 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 yellow amorphous product
  17. customThe amorphous product was purified by silica gel column chromatography (developing solution: hexane)

Sources & evidence

ORD record
ord-e18baff4d7f0491381b21b5dcbb20071
Source dataset
uspto-grants-2008_11
Patent number
US07449533B2

Reaction notes

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