Hydrochloric Acid → 1,2-bis(4,7-Dimethylindenyl)butane

HRID 1464351

Reaction equation

HRID 1464351 reaction equation
[CH2:1]([Li])[CH2:2][CH2:3][CH3:4].[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.Br[CH2:18][CH:19](Br)[CH2:20][CH3:21].Cl>CCCCCC.O1CCCC1>[CH3:4][C:3]1[CH:6]=[CH:7][C:8]([CH3:9])=[C:1]2[C:2]=1[CH:21]=[CH:20][CH:19]2[CH2:18][CH: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)[CH2:11][CH3:12]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 107921,2-DibromobutaneHCID 814584,7-dimethyl-1H-indeneHCID 178418339Butyllithium

Product 1

HCID 190879061,2-bis(4,7-Dimethylindenyl)butaneYield 10%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Conditions

Temperature
60 °C

Procedure

52 ml (83.2 mmol) of a 1.6 M solution of butyllithium in hexane were added dropwise to 11.8 g (92 mmol) of 4,7-dimethylindene in 200 ml of tetrahydrofuran at room temperature under an Ar atmosphere, and the mixture was stirred at 60° C. for 1 hour. It was cooled to -78° C., 5 ml (40 mmol) of 1,2-dibromobutane were added, and stirring was continued overnight at room temperature. The reaction mixture was poured onto 2 N aqueous HCl and the organic phase was separated off, washed with saturated aqueous NaHCO3 solution and NaCl solution in succession and dried (MgSO4). The oil which remained after the solvent had been stripped off under reduced pressure was chromatographed on 350 g of silica gel (hexane). After drying under an oilpump vacuum, 1.4 g (10%) of product were obtained.

Workup

  1. temperatureIt was cooled to -78° C.
  2. stirringstirring
  3. waitwas continued overnight at room temperature
  4. customthe organic phase was separated off
  5. washwashed with saturated aqueous NaHCO3 solution and NaCl solution in succession
  6. dry with materialdried (MgSO4)
  7. customwas chromatographed on 350 g of silica gel (hexane)
  8. customAfter drying under an oilpump vacuum

Sources & evidence

ORD record
ord-2702988df2984e0d8647bcb9044cc887
Source dataset
uspto-grants-1994_04
Patent number
US05304614

Linked notes

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