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Dichlorodimethylsilane → HCID 21943872, compound

HRID 2425311
Notes
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Reaction equation

HRID 2425311 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].[Li]CCCC.CCCCCC.[Si:24]([CH3:28])([CH3:27])(Cl)[Cl:25]>CCOCC.C1COCC1>[Cl:25][Si:24]([CH:3]1[C:4]2[C:9](=[C:8]([CH3:11])[CH:7]=[CH:6][C:5]=2[CH3:12])[CH:10]=[C:2]1[CH3:1])([CH3:28])[CH3:27]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 6398DichlorodimethylsilaneHCID 8058HexaneHCID 110626602,4,7-trimethyl-1H-indeneHCID 178418339Butyllithium

Product 1

HCID 21943872HCID 21943872, compoundYield 102.7%

Reagents, catalysts & solvents 2

HCID 3283Diethyl Ether
Solvent
2×
HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

7.24 g of 2,4,7 trimethylindene (45.8 mmol) were suspended in 70 ml of Et2O, cooled to 0° C., and to it were added 19.2 ml of a 2.5 M BuLi solution in hexane (48.0 mmol) with stirring. A slightly yellow cream is obtained. After allowing the reaction mixture to reach ambient temperature, additional 10 ml of Et2O were added, to improve stirring. After about 1 h the mixture was cooled again to 0° C. and 7.20 g of Me2SiCl2 (55.2 mmol, 1.2 eq) in 30 ml di THF, previously cooled to 0° C., were added to it. At the end of the addition, the reaction mixture was allowed to reach ambient temperature. At this point the reaction mixture, which appeared as a white suspension, was filtered to remove LiCl, and then all solvents and excess Me2SiCl2 were removed under reduced pressure to leave 11.8 g of pale yellow oil (98% yield).

Workup

  1. customA slightly yellow cream is obtained
  2. customto reach ambient temperature
  3. stirringto improve stirring
  4. temperatureAfter about 1 h the mixture was cooled again to 0° C.
  5. additionwere added to it
  6. additionAt the end of the addition
  7. customto reach ambient temperature
  8. filtrationwas filtered
  9. customto remove LiCl
  10. customall solvents and excess Me2SiCl2 were removed under reduced pressure

Sources & evidence

ORD record
ord-e7245a8d3da64edcabd0060a22589099
Source dataset
uspto-grants-2011_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07964679B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes