Water → 1-(4,7-Dimethyl-1-indenyl)-2-(4,7-dimethyl-1-indenyl)methyl benzene

HRID 321919Notes

Reaction equation

HRID 321919 reaction equation
[Li][CH2:2][CH2:3][CH2:4][CH3:5].[CH3:6][C:7]1[CH:15]=[CH:14][C:13]([CH3:16])=[C:12]2[C:8]=1[CH:9]=[CH:10][CH2:11]2.O>CCCCCC.C1COCC1.CCCCCC>[CH3:5][C:4]1[CH:11]=[CH:12][C:13]([CH3:16])=[C:2]2[C:3]=1[CH:2]=[CH:3][CH:4]2[C:5]1[CH:14]=[CH:15][CH:7]=[CH:8][C:9]=1[CH2:10][CH:11]1[C:12]2[C:8](=[C:7]([CH3:6])[CH:15]=[CH:14][C:13]=2[CH3:16])[CH:9]=[CH:10]1

Participants

6

Reactant 3

HCID 962WaterHCID 814584,7-dimethyl-1H-indeneHCID 178418339Butyllithium

Product 1

HCID 184717161-(4,7-Dimethyl-1-indenyl)-2-(4,7-dimethyl-1-indenyl)methyl benzene

Reagents, catalysts & solvents 2

HCID 8058HexaneSolventHCID 21883165Tetrahydrofuran hexaneSolvent2×

Conditions

Temperature
-70 °C

Procedure

4.12 ml (10.3 mmoles) of n-BuLi 2.5 M in hexane are added to a solution of 1.48 g of 4,7-dimethyl indene (XVIII) (10.3 mmoles; obtained as described above) in 55 ml of a mixture of THF-hexane 2/1. At the end of the addition, the mixture is left under stirring for 1 hour. It is then cooled to −70° C. and a solution of 2.3 g of the brominated compound having formula (XX) (7.37 mmoles) in THF/hexane are added dropwise. The mixture is left to rise to room temperature and is left to rest for 6 hours. It is then poured into water and is extracted with ethyl ether. The organic phase is washed until neutrality and dehydrated on sodium sulfate. The residue obtained by evaporation of the solvent is purified by silica gel chromatography eluating with petroleum ether. After evaporation of the eluant 2.0 g of the bis-indenyl ligand having formula (XXI) and indicated below, are obtained (72% yield).

Workup

  1. additionAt the end of the addition
  2. waitthe mixture is left
  3. additionare added dropwise
  4. waitThe mixture is left
  5. customto rise to room temperature
  6. waitis left
  7. waitto rest for 6 hours
  8. extractionis extracted with ethyl ether
  9. washThe organic phase is washed until neutrality
  10. customThe residue obtained by evaporation of the solvent
  11. customis purified by silica gel chromatography
  12. customAfter evaporation of the eluant 2.0 g of the bis-indenyl ligand
  13. customare obtained (72% yield)

Sources & evidence

ORD record
ord-5126c223f2b14f7bab136e8816d4a689
Source dataset
uspto-grants-2001_04
Patent number
US06211110B1

Reaction notes

Loading…