Hexane → HCID 178506829, compound
Reaction equation
[CH3:1][C:2]1[CH2:3][C:4]2[C:9]([CH:10]=1)=[C:8]([CH3:11])[CH:7]=[CH:6][C:5]=2[CH3:12].C([Li:17])CCC.CCCCCC>C1COCC1>[CH3:1][C:2]1[CH:10]([Li:17])[C:9]2[C:4]([CH:3]=1)=[C:5]([CH3:12])[CH:6]=[CH:7][C:8]=2[CH3:11]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of 2,4,7-trimethylindene (2.90 g, 18.3 mmol) in 50 ml of THF at 0° C. was added dropwise a 1.6 molar solution of butyllithium in hexane (11.45 ml, 18.3 mmol) in order to produce 2,4,7-trimethylindenyllithium. The solution was stirred for 6 h at room temperature and then added via a cannula to a solution of 1-(9-fluorenyl)-2-bromoethane (5.00 g, 18.3 mmol) in 30 ml THF cooled at -10° C. The mixture was stirred overnight at room temperature and then hydrolyzed with 50 ml of aqueous NH4Cl. The organic phase was separated and the aqueous layer was extracted with ether. The combined organic phases were dried on MgSO4, filtered and the solvent was removed. The residue was crystallized from hot 100% ethanol to give 1.86 g (29%) of 1-(9-fluorenyl)-2-[1-(2,4,7-trimethyl)indenyl]ethane precursor as a white solid; melting point 178-179° C.
Sources & evidence
- ORD record
- ord-0577fdd2240a4de4957ee40c222c2f7b
- Source dataset
- uspto-grants-2000_08
- Patent number
- US06100416
Reaction notes
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