Tributylstannane → 4,4-Dimethylhexanenitrile

HRID 1441039Notes

Reaction equation

HRID 1441039 reaction equation
C([SnH](CCCC)CCCC)CCC.Br[C:15]([CH3:19])([CH2:17][CH3:18])[CH3:16].[C:20](#[N:23])[CH:21]=[CH2:22]>C1C=CC=CC=1>[CH3:16][C:15]([CH3:19])([CH2:17][CH3:18])[CH2:22][CH2:21][C:20]#[N:23]

Participants

5

Reactant 3

HCID 5948TributylstannaneHCID 7855AcrylonitrileHCID 681802-Bromo-2-methylbutane

Product 1

HCID 224210484,4-Dimethylhexanenitrile

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

Tri n-butyl tin hydride (19.6 ml.) and α-azo-iso-butyronitrile (0.5 g.) were added succesively to a stirred solution of 2-bromo-2-methylbutane (10 g.) and acrylonitrile (43.5 ml.) in dry benzene (200 ml.). The mixture was heated at reflux for 6 hours, cooled and filtered. The residue was washed with diethyl ether (50 ml.) and the combined filtrates evaporated under reduced pressure. 4,4-Dimethylhexanenitrile was obtained as a colourless liquid (2.1 g.), b.p. 85°-94°/20 mm.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 6 hours
  3. temperaturecooled
  4. filtrationfiltered
  5. washThe residue was washed with diethyl ether (50 ml.)
  6. customthe combined filtrates evaporated under reduced pressure

Sources & evidence

ORD record
ord-24595ab858774dd5aea8dfad00a866a8
Source dataset
uspto-grants-1996_03
Patent number
US05502073

Reaction notes

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