Dichlorodimethylsilane → HCID 23295624, compound

HRID 1953957Notes

Reaction equation

HRID 1953957 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[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH:19]=[CH:18][CH:17]=1.C([Li])CCC.[Cl-].[Li+]>CCCCCC.O1CCCC1.C1(C)C=CC=CC=1>[CH3:1][Si:2]([Cl:3])([CH3:5])[CH:15]1[C:14]2[C:9](=[C:10]([C:16]3[C:25]4[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=4)[CH:19]=[CH:18][CH:17]=3)[CH:11]=[CH:12][CH:13]=2)[CH:8]=[C:7]1[CH3:6]

Participants

8

Reactant 4

HCID 6398DichlorodimethylsilaneHCID 433294Lithium ChlorideHCID 118072992-Methyl-7-(1-naphthyl)indeneHCID 178418339Butyllithium

Product 1

HCID 23295624HCID 23295624, compound

Reagents, catalysts & solvents 3

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent2×

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-(1-naphthyl)indenyllithium (i.e., a solution of 9.2 g (36 mmol) of 2-methyl-7-(1-naphthyl)indene in a mixed solvent of 75 ml of dry toluene and 5 ml of tetrahydrofuran 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 tetrahydrofuran) 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 dimethyldichlorosilane) were distilled off under reduced pressure at 8 mmHg to obtain dimethyl(2-methyl-4-(1-naphthyl)indenyl)silyl chloride.

Workup

  1. customdried over Na-K alloy), to which
  2. additionwas added a solution of 2-methyl-7-(1-naphthyl)indenyllithium (i.e.
  3. customprecipitated
  4. extractionthe supernatant was extracted with a syringe
  5. customtransferred into another flask
  6. distillationlow boiling components (solvent and unreacted dimethyldichlorosilane) were distilled off under reduced pressure at 8 mmHg

Sources & evidence

ORD record
ord-58835246293f48dd92774bd471a6474a
Source dataset
uspto-grants-2000_09
Patent number
US06121182

Reaction notes

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