Silane, trichloro(1,1-dimethylethyl)- → HCID 22114828, compound

HRID 374081Notes

Reaction equation

HRID 374081 reaction equation
[C:1]([Si:5]([Cl:8])(Cl)[Cl:6])([CH3:4])([CH3:3])[CH3:2].[Li][N:10]1[CH2:15][CH2:14][CH:13]([CH3:16])[CH2:12][CH2:11]1>C(OCC)C>[C:1]([Si:5]([N:10]1[CH2:15][CH2:14][CH:13]([CH3:16])[CH2:12][CH2:11]1)([Cl:8])[Cl:6])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 87494Silane, trichloro(1,1-dimethylethyl)-HCID 178506920HCID 178506920, compound

Product 1

HCID 22114828HCID 22114828, compoundYield 42.1%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

Under argon, a reaction vessel fitted with a stirrer was charged with 100 ml diethylether and 11.7 g. t-butyltrichlorosilane (0.0615 mol) and stirring was commenced. To this vessel was added dropwise 6.34 g 1-lithio-4-methylpiperidine in diethylether solution from (b) above via a cannula over a 30 min. period and stirring was continued for about 16 hours. The vessel was fitted with a condenser and the reaction mixture was refluxed for 1 hr. and cooled to room temperature. The solution was filtered through a medium porosity frit and the LiCl precipitate was washed three times with 20 ml portions of diethylether. The diethylether was removed from the filtrate in vacuo to provide a clear yellow oil. The crude product was distilled under vacuum (60°-68° C., @ 0.7 torr) to give a clear to slightly cloudy oil of 6.45 g of t-butyl(4methylpiperidyl)dichlorosilane.

Workup

  1. customUnder argon, a reaction vessel fitted with a stirrer
  2. customThe vessel was fitted with a condenser
  3. temperaturethe reaction mixture was refluxed for 1 hr
  4. filtrationThe solution was filtered through a medium porosity frit
  5. washthe LiCl precipitate was washed three times with 20 ml portions of diethylether
  6. customThe diethylether was removed from the filtrate in vacuo
  7. customto provide a clear yellow oil
  8. distillationThe crude product was distilled under vacuum (60°-68° C., @ 0.7 torr)

Sources & evidence

ORD record
ord-4cafc188cabb46608e2239a2f8b4f062
Source dataset
uspto-grants-1992_11
Patent number
US05166340

Reaction notes

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