Dibenzofuran → dibenzofuran-4-yl(triphenyl)silane

HRID 713593Notes

Reaction equation

HRID 713593 reaction equation
[CH:1]1[C:9]2[C:8]3[CH:10]=[CH:11][CH:12]=[CH:13][C:7]=3[O:6][C:5]=2[CH:4]=[CH:3][CH:2]=1.C(=O)=O.CC(O)C.C([Li])CCC.CCCCCC.Cl[Si:33]([C:46]1[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=1)([C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1>C1COCC1.CCOCC>[CH:1]1[C:9]2[C:8]3[CH:10]=[CH:11][CH:12]=[CH:13][C:7]=3[O:6][C:5]=2[C:4]([Si:33]([C:40]2[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=2)([C:46]2[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=2)[C:34]2[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=2)=[CH:3][CH:2]=1

Participants

8

Reactant 5

HCID 568DibenzofuranHCID 64581,1',1''-(Chlorosilylidyne)tris(benzene)HCID 8058HexaneHCID 86586944Isopropanol carbon dioxide2×HCID 178418339Butyllithium

Product 1

HCID 5084353dibenzofuran-4-yl(triphenyl)silaneYield 65%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

Dibenzo[b,d]furan (5.00 g, 29.7 mmol) was dissolved in THF (150 mL), and cooled in the CO2/i-PrOH bath. n-Butyllithium solution in hexane (2.5 M, 12.49 mL, 31.2 mmol) was added dropwise by syringe. After addition, it was stirred at room temperature for 2 hours, and cooled again in the CO2/i-PrOH bath. Chlorotriphenylsilane (8.77 g, 29.7 mmol) in ether (50 mL) was added dropwise into the reaction solution. The reaction was gradually warmed to room temperature and stirred overnight. After evaporation of the solvent, the crude product was purified by column chromatography on silica gel with DCM/hexane (1/9, v/v) as eluent to yield dibenzo[b,d]furan-4-yltriphenylsilane (8.2 g, 65%) as a white solid.

Workup

  1. additionAfter addition, it
  2. temperatureThe reaction was gradually warmed to room temperature
  3. stirringstirred overnight
  4. customAfter evaporation of the solvent
  5. customthe crude product was purified by column chromatography on silica gel with DCM/hexane (1/9, v/v) as eluent

Sources & evidence

ORD record
ord-2252b5bbe4584d0f8d8792bf767f3b4e
Source dataset
uspto-grants-2015_11
Patent number
US09184399B2

Reaction notes

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