Diethyl Ether → HCID 178504336, compound

HRID 379338Notes

Reaction equation

HRID 379338 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 8058HexaneSolvent2×

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 and, then, a hexane solution of n-butyllithium (30 mmol) was dropwise added at −10° C. with stirring over a period of 30 minutes. After the dropwise addition of the hexane solution, 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. Them, the slurry was dropwise added to a dichlorodimethylsilane (18.24 ml, 150 mmol)/dehydrated ether (100 nl) solution at −10° C. with stirring over a period of 1 hour. The temperature of the system was allowed to spontaneously rise to room temperature, followed by stirring over night. The reaction solution was filtered under pressure through a glass filter (G-5) to remove lithium chloride, and the solvent and the unreacted dichlorodimethylsilane remained in the filtrate were removed under reduced pressure. The resultant product was reslurried with dehydrated ether (100 ml) and the obtained slurry was filtered under pressure through a glass filter (C-5) to obtain 3.30 g of a white powder (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. customslowly rise to room temperature
  5. stirringby stirring at room temperature for 4 hours
  6. customThe reaction liquid
  7. stirringwith stirring over a period of 1 hour
  8. customto spontaneously rise to room temperature
  9. stirringby stirring over night
  10. filtrationThe reaction solution was filtered under pressure through a glass
  11. filtrationfilter (G-5)
  12. customto remove lithium chloride
  13. customwere removed under reduced pressure
  14. filtrationthe obtained slurry was filtered under pressure through a glass
  15. filtrationfilter (C-5)

Sources & evidence

ORD record
ord-f44fa3e47c03440285d976dd4766b2c3
Source dataset
uspto-grants-2001_10
Patent number
US06297333B1

Reaction notes

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