Chlorotrimethylsilane → 2,2'-Dilithiobiphenyl
Reaction equation
[C-]1[C:14]2[C:5](=C[C:7]3[C:12]([CH:13]=2)=[CH:11][CH:10]=[CH:9][CH:8]=3)[CH:4]=[CH:3][CH:2]=1.[Li+:15].[I-].[Ca+2].[I-].[Ca].Cl[Si](C)(C)C>>[C:12]1([C:13]2[CH:2]=[CH:3][CH:4]=[CH:5][C-:14]=2)[CH:11]=[CH:10][CH:9]=[CH:8][C-:7]=1.[Li+:15].[Li+:15]Participants
Procedure
Preformed lithium anthracenide was reacted with calcium iodide to prepare asoluble calcium species. This calcium species was added to chloromethylatedpolystyrene (DF=0.11) and stirred for 24 hours at room temperature. The corresponding calcium-substituted reagent was then reacted with chlorotrimethylsilane at room temperature to yield the silylated product; however, the yield was not optimized and was lower than the yield obtainedfrom preformed lithium biphenylide (Table III, entry 4). Reaction of the calcium species with chloromethylated polystyrene at 0° C. for 6 hours resulted in a 100% loss of chlorine from the polymer. Subsequent reaction with benzaldehyde gave the corresponding secondary alcohol in 80%yield, compared to the 100% yield when calcium biphenylide was used (Table III, entry 6).
Workup
- customto yield the silylated product
Sources & evidence
- ORD record
- ord-be13d9bdd0a24fbaac738f1cc510f859
- Source dataset
- uspto-grants-1994_07
- Patent number
- US05330687
Reaction notes
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