1,1',1''-(Chlorosilylidyne)tris(benzene) → (9H-Fluoren-9-yl)(triphenyl)silane

HRID 2373083Notes

Reaction equation

HRID 2373083 reaction equation
[CH:1]1[C:13]2[CH2:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.C([Li])CCC.[C:19]1([Si:25](Cl)([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>CCOCC.C1C=CC=CC=1>[C:32]1([Si:25]([C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH:12]2[C:11]3[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=3[C:5]3[C:13]2=[CH:1][CH:2]=[CH:3][CH:4]=3)[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=1

Participants

6

Reactant 3

HCID 64581,1',1''-(Chlorosilylidyne)tris(benzene)HCID 6853FluoreneHCID 178418339Butyllithium

Product 1

HCID 12666783(9H-Fluoren-9-yl)(triphenyl)silaneYield 98.9%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 3283Diethyl EtherSolvent

Procedure

To a solution of 17 g of fluorene (102.4 mmol) in 300 mL of dry ether was added 46 mL of 2.3M n-butyllithium dropwise over a period of 20 minutes. The mixture was refluxed for 3 hours, cooled in an ice bath, and treated in one portion with a solution of 24 g (81.46 mmol) of triphenylsilyl chloride in 100 mL of dry benzene. The mixture was refluxed for 24 hours, cooled to room temperature, and washed with sat'd NH4Cl (100 mL), brine (150 mL), and water (150 mL). The organic layer was dried over MgSO4 and the solvent was evaporated in vacuo to give a yellow residue which was triturated with methanol to afford 34.18 g (98.9%) of the crude silane as an off-white solid. Recrystallization from EtOAc--EtOH (4:1) gave 27.46 g (79.5%) of the pure triphenylsilane as white needles, m.p. 182°-193° C.; 1H NMR (CDCl3): δ 4.72 (s, 1H, CH), 6.82-7.90 (m, 23H, aryl).

Workup

  1. temperatureThe mixture was refluxed for 3 hours
  2. temperaturecooled in an ice bath
  3. temperatureThe mixture was refluxed for 24 hours
  4. washwashed with sat'd NH4Cl (100 mL), brine (150 mL), and water (150 mL)
  5. dry with materialThe organic layer was dried over MgSO4
  6. customthe solvent was evaporated in vacuo
  7. customto give a yellow residue which
  8. customwas triturated with methanol

Sources & evidence

ORD record
ord-795702c0abd543f682068277b16f7895
Source dataset
uspto-grants-1992_03
Patent number
US05101059

Reaction notes

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