Diethyl Ether → HCID 178504336, compound

HRID 379340Notes

Reaction equation

HRID 379340 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-neck 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 mmol) was dropwise added over a period of 30 minutes. After the dropwise addition, the temperature of the system was allowed to spontaneously and slowly rise to room temperature, followed by stirring at room temperature for 4 hours. The reaction, liquid became a yellow slurry. The slurry was dropwise added to a dichlorodimehylsilane (18.24 ml, 150 mmol)/dehydrated ether (100 ml) solution under stirring at −10° C. over a period of 1 hour. 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-neck 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. customslowly rise to room temperature
  6. stirringby stirring at room temperature for 4 hours
  7. customThe reaction, liquid
  8. stirringunder stirring at −10° C. over a period of 1 hour
  9. customwas allowed to spontaneously rise to room temperature
  10. stirringthe reaction mixture was stirred over night
  11. customLithium chloride was removed by means of pressure filteration of the resulting solution
  12. filtrationfilter (G-5)
  13. customwere removed under reduced pressure
  14. filtrationfilter (G-5)

Sources & evidence

ORD record
ord-f38409470911460580962e28e592439a
Source dataset
uspto-grants-2001_10
Patent number
US06297333B1

Reaction notes

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