Fluorene → HCID 19902687, compound

HRID 2373084Notes

Reaction equation

HRID 2373084 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.C1COCC1.C([Li])CCC.[CH:24]([Si:27](Cl)([CH:31]([CH3:33])[CH3:32])[CH:28]([CH3:30])[CH3:29])([CH3:26])[CH3:25]>CCOCC>[CH:24]([Si:27]([CH:31]([CH3:33])[CH3:32])([CH:28]([CH3:30])[CH3:29])[CH:12]1[C:11]2[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=2[C:5]2[C:13]1=[CH:1][CH:2]=[CH:3][CH:4]=2)([CH3:26])[CH3:25]

Participants

6

Reactant 4

HCID 6853FluoreneHCID 8028TetrahydrofuranHCID 139400Triisopropylsilyl chlorideHCID 178418339Butyllithium

Product 1

HCID 19902687HCID 19902687, compoundYield 73.9%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution of 3.0 g (18.07 mmol) of fluorene in 50 mL of dry ether and 25 mL of freshly distilled THF was added dropwise 13 mL of 1.4M n-butyllithium. The mixture was refluxed for 3 hours, cooled to room temperature, and treated with 3 mL (14.02 mmol) of triisopropylsilyl chloride in one portion. The mixture was refluxed for 3 days, cooled to room temperature, and washed with sat'd NH4Cl (2×50 mL) and water (50 mL). The organic layer was dried over MgSO4 and the solvent was evaporated in vacuo to give an oil which was triturated with methanol to afford 3.34 g (73.8%) of the crude silane as a yellowish solid. Recrystallization from EtOH gave 2.98 g (65.9%) of 9-triisopropylsilylfluorene as white needles, m.p. 122°-123° C.; 1H NMR (CDCl3): δ 0.91 (d, 18H, Si-C-Me2), 1.09-1.42 (hept, 3H, Si-CH-Me2 , 4.26 s, 1H, ArCHAr), 7.05-8.00 (m, 8H, aryl).

Workup

  1. temperatureThe mixture was refluxed for 3 hours
  2. temperatureThe mixture was refluxed for 3 days
  3. temperaturecooled to room temperature
  4. washwashed with sat'd NH4Cl (2×50 mL) and water (50 mL)
  5. dry with materialThe organic layer was dried over MgSO4
  6. customthe solvent was evaporated in vacuo
  7. customto give an oil which
  8. customwas triturated with methanol

Sources & evidence

ORD record
ord-28dc080b19a340dab490a5bb20e7d550
Source dataset
uspto-grants-1992_03
Patent number
US05101059

Reaction notes

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