Water → HCID 131722726, compound

HRID 1383697Notes

Reaction equation

HRID 1383697 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.[CH2:14]([Li])[CH2:15][CH2:16][CH3:17].O.C(O[CH2:23][CH3:24])C>C1COCC1.CCCCCC>[C:1]1([CH2:17][CH:16]([CH:24]2[CH:23]=[CH:11][CH:6]=[CH:7]2)[CH2:15][CH2:14][CH2:5][CH2:13][CH2:1][CH2:2][CH2:3][CH3:4])[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

Participants

7

Reactant 4

HCID 962WaterHCID 3283Diethyl EtherHCID 6853FluoreneHCID 178418339Butyllithium

Product 1

HCID 131722726HCID 131722726, compoundYield 38%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Procedure

19.0 g (114 mmol) of fluorene was introduced into a flask under a high purity argon atmosphere and dissolved in 200 ml of THF. 50.2 ml of 2.5 N n-butyl lithium (n-BuLi) in hexane was slowly added thereto at −78° C. The mixture was slowly warmed to room temperature and then stirred for another 2 hours. 11.7 of spiro (2-octylcyclopropane)-1,1′-cyclopentadiene diluted in 200 ml of THF was added dropwise thereto at 0° C., and then stirred for 24 hours at room temperature. 200 ml of water and 500 ml of diethyl ether were added to the reaction mixture, agitated and the organic layer was separated and dried on anhydrous magnesium sulfate. After removing magnesium sulfate by filtration, the solvent was evaporated under a reduced pressure and the residue was subjected to silica gel column chromatography (eluent: hexane) to obtain 8.1 g of pure 1-fluorenyl-2-cyclopentadienyldecane (Yield: 38%).

Workup

  1. customat −78° C
  2. additionwas added dropwise
  3. stirringat 0° C., and then stirred for 24 hours at room temperature
  4. stirringagitated
  5. customthe organic layer was separated
  6. dry with materialdried on anhydrous magnesium sulfate
  7. customAfter removing magnesium sulfate
  8. filtrationby filtration
  9. customthe solvent was evaporated under a reduced pressure

Sources & evidence

ORD record
ord-ee9cbdd5af8f463285080dddbdb538b3
Source dataset
uspto-grants-2001_07
Patent number
US06255417B1

Reaction notes

Loading…