4,7-dimethyl-1H-indene → HCID 178506817, compound

HRID 432885Notes

Reaction equation

HRID 432885 reaction equation
[CH3:1][C:2]1[CH:10]=[CH:9][C:8]([CH3:11])=[C:7]2[C:3]=1[CH:4]=[CH:5][CH2:6]2.C([Li:16])CCC>O1CCCC1>[CH3:1][C:2]1[CH:10]=[CH:9][C:8]([CH3:11])=[C:7]2[C:3]=1[CH:4]=[CH:5][CH:6]2[Li:16]

Participants

4

Reactant 2

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

Product 1

HCID 178506817HCID 178506817, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

38.2 g (265 mmol) of 4,7-dimethylindene were dissolved in 350 ml of tetrahydrofuran, and the temperature of the solution was taken to 0° C. 165 ml of n-butyllithium (1.6 M in hexane, 264 mmol) were then added dropwise drop over 2.5 hours. After returning to room temperature and continued stirring for 4 hours, a red-purple solution of 4,7-dimethylindenyllithium was obtained. This solution was cooled to −70° C. and treated dropwise in the course of 35 minutes with 25.3 g of 1,2-dibromoethane (135 mmol) in 15 ml of tetrahydrofuran. After returning to room temperature, this gave a clear yellow solution, to which water was added. The organic phase was collected and dried over Na2SO4. The solvent was then evaporated in vacuum, 20 g of product (48% yield) being obtained.

Workup

  1. customwas taken to 0° C
  2. customAfter returning to room temperature

Sources & evidence

ORD record
ord-396ba1990a0c4a85be2e6babd6230814
Source dataset
uspto-grants-2003_12
Patent number
US06664351B1

Reaction notes

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