3-Trimethylsilylpropanoyl chloride → 4,4-Dimethyl-4-silapentanoyl cyanide

HRID 1440991Notes

Reaction equation

HRID 1440991 reaction equation
[CH3:1][Si:2]([CH3:9])([CH3:8])[CH2:3][CH2:4][C:5](Cl)=[O:6].[Cu][C:11]#[N:12]>C(Cl)Cl>[CH3:1][Si:2]([CH3:9])([CH3:8])[CH2:3][CH2:4][C:5]([C:11]#[N:12])=[O:6]

Participants

4

Reactant 2

HCID 5644893-Trimethylsilylpropanoyl chlorideHCID 178418546HCID 178418546, compound

Product 1

HCID 153324834,4-Dimethyl-4-silapentanoyl cyanideYield 30.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In a flask were placed 5.0 g (0.032 mole) of 4,4-dimethyl-4-silapentanoic acid chloride and 2.89 g (0.032 mole) of copper(I) cyanide. This mixture was heated at approximately 150°-200° C. for a period of 50 minutes after which it was cooled to ambient temperature. Methylene chloride was added to the reaction mixture which was then filtered. The solvent was evaporated from the filtrate under reduced pressure, leaving 1.5 g of 4,4-dimethyl-4-silapentanoyl cyanide as a residue.

Workup

  1. customIn a flask were placed
  2. temperatureThis mixture was heated at approximately 150°-200° C. for a period of 50 minutes after which it
  3. filtrationwas then filtered
  4. customThe solvent was evaporated from the filtrate under reduced pressure

Sources & evidence

ORD record
ord-e4b67204096c4d50b7fe693b282ac2ca
Source dataset
uspto-grants-1996_03
Patent number
US05502054

Reaction notes

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