Tetrahydrofuran → (Cyclopentadienyl)(fluorenyl)methane

HRID 1613025Notes

Reaction equation

HRID 1613025 reaction equation
ClCC1([Si](C)(C)C)[C:15]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[C:9]2[C:4]1=[CH:5][CH:6]=[CH:7][CH:8]=2.[CH:20]1([Li])[CH:24]=[CH:23][CH:22]=C1.O1C[CH2:29][CH2:28][CH2:27]1>>[CH:14]1([CH2:13][C:12]2[C:11]3[CH2:10][C:9]4[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=4)[C:22]=3[CH:23]=[CH:24][CH:20]=2)[CH:15]=[CH:29][CH:28]=[CH:27]1

Participants

4

Reactant 3

HCID 8028Tetrahydrofuran2×HCID 194336909-(Chloromethyl)-9-(trimethylsilyl)fluoreneHCID 178506819HCID 178506819, compound

Product 1

HCID 131717798(Cyclopentadienyl)(fluorenyl)methane

Procedure

The 9-(chloromethyl)-9-(trimethylsilyl) fluorene was dissolved in 200 ml tetrahydrofuran and added dropwise to a solution of cyclopentadienyl lithium (0.04 m) in 200 ml of tetrahydrofuran. The reaction mixture was stirred for another 2 hours. The yellow solution was washed with 50 ml of an aqueous NH4Cl solution, then washed with 50 ml of water, and then the organic phase was dried over Na2SO4. Then the solvent was removed in vacuo. The raw product was dissolved in pentane and was crystallized at -30° C. The recovered product is 1-fluorenyl-1-cyclopentadienyl methane.

Workup

  1. washThe yellow solution was washed with 50 ml of an aqueous NH4Cl solution
  2. washwashed with 50 ml of water
  3. dry with materialthe organic phase was dried over Na2SO4
  4. customThen the solvent was removed in vacuo
  5. dissolutionThe raw product was dissolved in pentane
  6. customwas crystallized at -30° C

Sources & evidence

ORD record
ord-552b6aea2de1427f98625449edf68baf
Source dataset
uspto-grants-1993_03
Patent number
US05191132

Reaction notes

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