Dichlorodimethylsilane → Dimethyl(2-methyl-4-phenylindenyl)silyl chloride
Reaction equation
[CH3:1][Si:2]([CH3:5])(Cl)[Cl:3].[CH3:6][C:7]1[CH2:8][C:9]2[C:14]([CH:15]=1)=[CH:13][CH:12]=[CH:11][C:10]=2[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C([Li])CCC.[Cl-].[Li+]>CCCCCC.C(OCC)C.C1COCC1>[CH3:1][Si:2]([Cl:3])([CH3:5])[CH:15]1[C:14]2[C:9](=[C:10]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH:11]=[CH:12][CH:13]=2)[CH:8]=[C:7]1[CH3:6]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 3
Procedure
23 g (180 mmol) of dimethyldichlorosilane was dissolved in 200 ml of dry n-hexane (dried over Na-K alloy), to which was added a solution of 2-methyl-7-phenylindenyllithium (i.e., a solution of 7.4 g (36 mmol) of 2-methyl-7-phenylindene in 70 ml of dry diethyl ether to which was dripped down 22.5 ml of a 1.6 M hexane solution of n-butyllithium at -78° C., followed by stirring at room temperature for 3 hours and by addition of 50 ml of THF) under ice cooling. The mixture was stirred as was at room temperature for 3 hours to deposit white salt of lithium chloride. After standing the mixture so that the white salt precipitated, the supernatant was extracted with a syringe and transferred into another flask and low boiling components (solvent and unreacted dimethyidichlorosilane) were distilled off under reduced pressure at 8 mmHg to obtain dimethyl(2-methyl-4-phenylindenyl)silyl chloride.
Workup
- customdried over Na-K alloy), to which
- additionwas added a solution of 2-methyl-7-phenylindenyllithium (i.e.
- customprecipitated
- extractionthe supernatant was extracted with a syringe
- customtransferred into another flask
- distillationlow boiling components (solvent and unreacted dimethyidichlorosilane) were distilled off under reduced pressure at 8 mmHg
Sources & evidence
- ORD record
- ord-7eff039c45ab48d484e2cf89b4e81cd9
- Source dataset
- uspto-grants-2000_09
- Patent number
- US06121182
Reaction notes
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