Diethyl Ether → HCID 178504336, compound

HRID 379336Notes

Reaction equation

HRID 379336 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.CCOCC.C([Li])CCC.[Cl:24][Si:25](Cl)([CH3:27])[CH3:26]>CCCCCC>[Cl-:24].[CH3:26][SiH:25]([CH3:27])[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

6

Reactant 4

HCID 3283Diethyl Ether2×HCID 6398DichlorodimethylsilaneHCID 6853FluoreneHCID 178418339Butyllithium

Product 1

HCID 178504336HCID 178504336, compoundYield 43%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Conditions

Temperature
-10 °C

Procedure

A 1 liter four-necked flask equipped with a reflux tube, a thermometer and a dropping funnel was thoroughly purged with nitrogen and dried. To the flask, fluorene (5.00 g, 30 mmol) and dehydrated ether (100 ml) were introduced. Under stirring at −10° C., a hexane solution of n-butyllithium (30 Tmol) was dropwise added over a period of 30 minutes. After the dropwise addition, the temperature of the system was allowed to spontaneously rise to room temperature little by little, and the reaction mixture was stirred at room temperature for 4 hours. The reaction solution turned into a yellow slurry. The slurry was dropwise added to a solution of dichlorodimethylsilane (18.24 ml, 150 mmol)/dehydrated ether (100 ml) over a period of 1 hour under stirring at ˜10° C. After the temperature of the system was allowed to spontaneously rise to room temperature, the reaction mixture was stirred over night. Lithium chloride was removed by means of pressure filteration of the resulting solution using a glass filter (G-5). Further the solvent and the unreacted dichlorodimethylsilane remained in the filtrate were removed under reduced pressure. The resulting filtrate was reslurried with dehydrated hexane (100 ml) and subjected to pressure filteration using a glass filter (G-5) to obtain a white powder (3.30 g, yield: 43%).

Workup

  1. customA 1 liter four-necked flask equipped with a reflux tube
  2. customa thermometer and a dropping funnel was thoroughly purged with nitrogen
  3. customdried
  4. additionAfter the dropwise addition
  5. customto spontaneously rise to room temperature
  6. stirringwas stirred at room temperature for 4 hours
  7. stirringunder stirring at ˜10° C
  8. customwas allowed to spontaneously rise to room temperature
  9. stirringthe reaction mixture was stirred over night
  10. customLithium chloride was removed by means of pressure filteration of the resulting solution
  11. filtrationfilter (G-5)
  12. customwere removed under reduced pressure
  13. filtrationfilter (G-5)

Sources & evidence

ORD record
ord-704d7a2c99874fd7af14da8fc0645c2e
Source dataset
uspto-grants-2001_10
Patent number
US06297333B1

Reaction notes

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