4,7-dimethyl-1H-indene → HCID 178506817, compound
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
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
38.2 g (265 mmol) of 4,7-dimethylindene were dissolved in 350 ml of tetrahydrofuran and the temperature of the solution was raised to 0° C. Thereafter, 165 ml of n-butyl-lithium (1.6M in hexane, 264 mmol) were added dropwise over 2.5 hours. After having allowed the whole to again reach room temperature and whilst stirring for 4 hours, a purple-red solution of 4,7-dimethylindenyllithium was obtained. This solution was cooled to −70° C. and treated, dropwise for 35 minutes, with 25.3 g of 1,2-dibromethane (135 mmol) in 15 ml of tetrahydrofuran. After the temperature was raised again to room temperature, a light yellow solution was obtained to which water was added. The organic phase was collected and dried on Na2SO4. The solvent was then evaporated under vacuum and 20 g of product (yield 48%) were obtained.
Workup
- customwhole to again reach room temperature
Sources & evidence
- ORD record
- ord-cac2c426618943b8a3cfe6d4d1c9914d
- Source dataset
- uspto-grants-2002_09
- Patent number
- US06444604B1
Reaction notes
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