Ethylenediamine → 2,3,4,9-Tetrahydro-1H-fluorene

HRID 1256863Notes

Reaction equation

HRID 1256863 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.C(N)CN.C1COCC1.[Li]>O>[CH2:10]1[C:11]2[CH2:12][C:13]3[C:5](=[CH:4][CH:3]=[CH:2][CH:1]=3)[C:6]=2[CH2:7][CH2:8][CH2:9]1

Participants

6

Reactant 4

HCID 3301EthylenediamineHCID 6853FluoreneHCID 8028TetrahydrofuranHCID 3028194Lithium

Product 1

HCID 5884652,3,4,9-Tetrahydro-1H-fluoreneYield 90.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

30 g (0.18 mol) of fluorene was placed in a 1 L glass vessel, to which a mixed solution of 175 mL of ethylenediamine and 175 mL of THF was added under a nitrogen atmosphere, and dissolved by stirring. 5.6 g (0.812 mol) of metallic lithium was added to the resulting solution at 0° C. over 50 minutes. After completing the reaction, water was added thereto, and the target compound was extracted with diethyl ether and rinsed with a sodium chloride aqueous solution. Magnesium sulfate was added to the diethyl ether layer, which was dried in a refrigerator overnight. Magnesium sulfate was filtered off, and diethyl ether was removed to provide 27.6 g of 1,2,3,4-tetrahydrofluorene (4HFluH) as an orange solid matter (yield: 90%).

Workup

  1. dissolutiondissolved
  2. additionwas added
  3. extractionthe target compound was extracted with diethyl ether
  4. washrinsed with a sodium chloride aqueous solution
  5. additionMagnesium sulfate was added to the diethyl ether layer, which
  6. customwas dried in a refrigerator overnight
  7. filtrationMagnesium sulfate was filtered off
  8. customdiethyl ether was removed

Sources & evidence

ORD record
ord-dc033bbddf9b44d8b1e0e917717983a2
Source dataset
uspto-grants-2013_06
Patent number
US08461270B2

Reaction notes

Loading…