Fluorene → HCID 19978437, compound

HRID 1089825Notes

Reaction equation

HRID 1089825 reaction equation
[Li]CCCC.[CH:6]1[C:18]2[CH2:17][C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[C:10]=2[CH:9]=[CH:8][CH:7]=1.Br[CH2:20][CH2:21][CH:22]1[O:26][CH2:25][CH2:24][O:23]1.CCOC(C)=O>C1COCC1.CCCCCC>[CH2:21]([C:22]1([CH:17]2[C:16]3[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=3[C:10]3[C:18]2=[CH:6][CH:7]=[CH:8][CH:9]=3)[O:26][CH2:25][CH2:24][O:23]1)[CH3:20]

Participants

7

Reactant 4

HCID 6853FluoreneHCID 8857Ethyl AcetateHCID 877762-(2-Bromoethyl)-1,3-dioxolaneHCID 178418339Butyllithium

Product 1

HCID 19978437HCID 19978437, compoundYield 52%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Procedure

A solution of BuLi (2.35 M in hexane, 25.6 mL, 60.2 mmol) was slowly added into a cooled (-78° C.) solution of fluorene (10 g, 60.2 mmol) in 200 mL THF. The reaction mixture turned dark red and solid started to precipitate out. After 30 minutes 2-(2-bromoethyl)-1,3-dioxolane (12 g, 66.3 mmol) was added to the cold solution and the solution was warmed up to room temperature. TLC (silica, 5% EtOAc in hexane) was used to monitor the reaction. After two hours the reaction was quenched with water and the product was extracted into EtOAc. The organic layer was washed with water (×3), dried over magnesium sulfate and evaporated. Short path chromatography afforded 8.34 g (52%) of the product as a colorless oil.

Workup

  1. customto precipitate out
  2. customthe reaction
  3. customAfter two hours the reaction was quenched with water
  4. extractionthe product was extracted into EtOAc
  5. washThe organic layer was washed with water (×3)
  6. dry with materialdried over magnesium sulfate
  7. customevaporated

Sources & evidence

ORD record
ord-6c2e3f808de24506946758c82f572621
Source dataset
uspto-grants-1992_01
Patent number
US05079260

Reaction notes

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