Chlorotrimethylsilane → 1,3-Cyclopentadiene, (trimethylsilyl)-
Reaction equation
[CH3:1][Si:2](Cl)([CH3:4])[CH3:3].[CH:6]1([Na])[CH:10]=[CH:9][CH:8]=[CH:7]1>O1CCCC1>[CH3:1][Si:2]([C:7]1[CH2:6][CH:10]=[CH:9][CH:8]=1)([CH3:4])[CH3:3]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -78 °C
Procedure
11 g of trimethylsilyl chloride was dissolved in 30 mol of well dried tetrahydrofuran in a 300 ml flask whose inside had been substituted by nitrogen, and the obtained solution was cooled to −78° C. 100 ml of a tetrahydrofuran solution (2.0 mol/l) of cyclopentadienyl sodium was added dropwise to the above solution in a stream of nitrogen over 1 hour. The solution was stirred at −78° C. for 1 hour and returned to room temperature over 6 hours. A salt precipitated in the mixture solution was removed by filtration in a nitrogen atmosphere, and the residual solution was distilled to obtain 8 g of trimethylsilyl cyclopentadiene.
Workup
- waitreturned to room temperature over 6 hours
- customA salt precipitated in the mixture solution
- customwas removed by filtration in a nitrogen atmosphere
- distillationthe residual solution was distilled
Sources & evidence
- ORD record
- ord-8af64c012b31467698caaf0202fc5dfe
- Source dataset
- uspto-grants-2007_07
- Patent number
- US07238822B2
Reaction notes
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