Chlorotrimethylsilane → 1-(3-Trimethylsilylcyclopentadienyl)-1-(3,6-di-tert-butylfluorenyl)diphenylmethane

HRID 271014Notes

Reaction equation

HRID 271014 reaction equation
[CH:1]1([C:6]([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[C:7]2[C:19]3[CH2:18][C:17]4[C:12](=[CH:13][C:14]([C:20]([CH3:23])([CH3:22])[CH3:21])=[CH:15][CH:16]=4)[C:11]=3[CH:10]=[C:9]([C:24]([CH3:27])([CH3:26])[CH3:25])[CH:8]=2)[CH:5]=[CH:4][CH:3]=[CH:2]1.CCCCCC.C([Li])CCC.Cl[Si:52]([CH3:55])([CH3:54])[CH3:53]>C1COCC1.O>[CH3:53][Si:52]([CH3:55])([CH3:54])[C:3]1[CH:4]=[CH:5][CH:1]([C:6]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[C:7]2[C:19]3[CH2:18][C:17]4[C:12](=[CH:13][C:14]([C:20]([CH3:23])([CH3:22])[CH3:21])=[CH:15][CH:16]=4)[C:11]=3[CH:10]=[C:9]([C:24]([CH3:26])([CH3:27])[CH3:25])[CH:8]=2)[CH:2]=1

Participants

7

Reactant 4

HCID 6397ChlorotrimethylsilaneHCID 8058HexaneHCID 1317251321-(Cyclopentadienyl)-1(3,6-di-tert-butylfluorenyl)diphenylmethaneHCID 178418339Butyllithium

Product 1

HCID 1317251331-(3-Trimethylsilylcyclopentadienyl)-1-(3,6-di-tert-butylfluorenyl)diphenylmethaneYield 82.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 0.45 g (0.88 mmol) of 1-(cyclopentadienyl)-1(3,6-di-tert-butylfluorenyl)diphenylmethane in 30 ml of THF, 0.54 ml (0.97 mmol) of a hexane solution of n-butyllithium was dropwise added in a nitrogen atmosphere with ice cooling, followed by stirring at room temperature for 16 hours. After the resulting solution was cooled to −78° C., a solution of 0.22 ml (1.76 mmol) of chlorotrimethylsilane in 10 ml of THF was slowly added, followed by stirring at room temperature for 6 hours. To the reaction solution, 20 ml of water was added to terminate the reaction. The resulting solution was subjected to extraction with diethyl ether, then dried over anhydrous magnesium sulfate and vacuum evaporated to dryness to obtain a yellow solid. The solid was washed with a small amount of methanol and dried under reduced pressure to obtain 0.42 g of an opaque white solid (yield: 81.8%) The analyzed values are given below.

Workup

  1. temperatureAfter the resulting solution was cooled to −78° C.
  2. stirringby stirring at room temperature for 6 hours
  3. customto terminate
  4. customthe reaction
  5. extractionThe resulting solution was subjected to extraction with diethyl ether
  6. dry with materialdried over anhydrous magnesium sulfate and vacuum
  7. customevaporated to dryness
  8. customto obtain a yellow solid
  9. washThe solid was washed with a small amount of methanol
  10. customdried under reduced pressure

Sources & evidence

ORD record
ord-5567a0b9d6aa45e091e3e8a6a8e06a90
Source dataset
uspto-grants-2008_11
Patent number
US07449533B2

Reaction notes

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