Chlorotrimethylsilane → 9-(TRIMETHYLSILYL)FLUORENE

HRID 275505Notes

Reaction equation

HRID 275505 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.Cl[Si:20]([CH3:23])([CH3:22])[CH3:21].[NH4+].[Cl-]>O1CCCC1.O>[CH3:21][Si:20]([CH3:23])([CH3:22])[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

Participants

7

Reactant 4

HCID 6397ChlorotrimethylsilaneHCID 6853FluoreneHCID 25517Ammonium ChlorideHCID 178418339Butyllithium

Product 1

HCID 5535709-(TRIMETHYLSILYL)FLUORENE

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

First, 8.3 g (0.05 m) of fluorene was dissolved in 150 ml of tetrahydrofuran. Then 31.8 ml (0.05 m) of butyl lithium (1.6 molar in hexane) was added dropwise to this solution. After a stirring period of one hour, 6.3 ml (0.05 mol) of chlorotrimethylsilane, dissolved in 25 ml of tetrahydrofuran was added to this solution over 3 hours. The reaction mixture was stirred for an additional 3 hours. Then, 50 ml of an aqueous NH4Cl solution was added to the dark yellow solution. The solution was treated with 50 ml of water. The organic phase was dried over Na2SO4. Then the solvent was removed in vacuo. The yellow residue was dissolved in pentane. The product 9-(trimethylsilyl)fluorene was crystallized at 4° C. A yield of 8.33 g was obtained.

Workup

  1. additionwas added to this solution over 3 hours
  2. dry with materialThe organic phase was dried over Na2SO4
  3. customThen the solvent was removed in vacuo
  4. dissolutionThe yellow residue was dissolved in pentane
  5. customThe product 9-(trimethylsilyl)fluorene was crystallized at 4° C
  6. customA yield of 8.33 g was obtained

Sources & evidence

ORD record
ord-493cbb7363f84758be0f37b29dff46c1
Source dataset
uspto-grants-1995_02
Patent number
US05393911

Reaction notes

Loading…