Dichlorodimethylsilane → HCID 131725932, compound

HRID 2213696Notes

Reaction equation

HRID 2213696 reaction equation
[CH3:1][C:2]1[CH2:3][C:4]2[CH:5]=[CH:6][C:7]3[CH:15]=[CH:14][CH:13]=[CH:12][C:8]=3[C:9]=2[C:10]=1[Li].[CH3:16][Si:17]([CH3:20])(Cl)[Cl:18]>O1CCCC1.C(OCC)C>[CH3:1][C:2]1[CH2:3][C:4]2[CH:5]=[CH:6][C:7]3[CH:15]=[CH:14][CH:13]=[CH:12][C:8]=3[C:9]=2[C:10]=1[Si:17]([CH3:20])([CH3:16])[Cl:18]

Participants

4

Reactant 2

HCID 6398DichlorodimethylsilaneHCID 178506669HCID 178506669, compound2×

Product 1

HCID 131725932HCID 131725932, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 21868444Ether tetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

The thus-obtained white solid (2-methylbenzo[e]indenyllithium, 0.94 g, 5.1 mmols) was dissolved in dry tetrahydrofuran/diethyl ether (40 ml, 1/1 v/v). On the other hand, dimethyldichlorosilane (2.60 g, 20.2 mmols) was dissolved in dry tetrahydrofuran/diethyl ether (20 ml, 1/1 v/v), and the resulting solution was dropwise added to the previously-prepared 2-methylbenzo[e]indenyllithium solution at −5° C., over 1 hour. After the addition, this was immediately warmed up to 0° C. with stirring, and further stirred at room temperature for 2 hours. The solvent was removed from the pale yellow suspension under reduced pressure to obtain a yellow paste. The paste was extracted with dry diethyl ether (10 ml×3), and the resulting solution was filtered through a cannula. The filtrate was collected, the solvent was removed under reduced pressure, and this was dried under reduced pressure until it had a constant weight. The thus-obtained viscous yellow oil is 2-methylbenzo[e]indenyldimethylchorosilane (1.35 g, yield 100%).

Workup

  1. additionAfter the addition
  2. stirringfurther stirred at room temperature for 2 hours
  3. customThe solvent was removed from the pale yellow suspension under reduced pressure
  4. customto obtain a yellow paste
  5. extractionThe paste was extracted with dry diethyl ether (10 ml×3)
  6. filtrationthe resulting solution was filtered through a cannula
  7. customThe filtrate was collected
  8. customthe solvent was removed under reduced pressure
  9. customthis was dried under reduced pressure until it

Sources & evidence

ORD record
ord-0505c9d55fd743d3a0cd179be6af4a26
Source dataset
uspto-grants-2006_09
Patent number
US07105604B2

Reaction notes

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