Sodium Iodide → Silane, (6-iodo-1-hexynyl)trimethyl-

HRID 1494665Notes

Reaction equation

HRID 1494665 reaction equation
Cl[CH2:2][CH2:3][CH2:4][CH2:5][C:6]#[C:7][Si:8]([CH3:11])([CH3:10])[CH3:9].[I-:12].[Na+]>CC(=O)CC>[I:12][CH2:2][CH2:3][CH2:4][CH2:5][C:6]#[C:7][Si:8]([CH3:11])([CH3:10])[CH3:9]

Participants

4

Reactant 2

HCID 5238Sodium IodideHCID 13839479(6-Chlorohex-1-yn-1-yl)trimethylsilane

Product 1

HCID 10401411Silane, (6-iodo-1-hexynyl)trimethyl-Yield 96.2%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

A mixture of 6-chloro-1-trimethylsilylhex-1-yne (14.0 g.) and sodium iodide (30 g) in butanone (100 ml) was heated at reflux, with stirring, for 10 hours. After this time the solvent was removed in vacuo and the residue partitioned between diethyl ether and water. The organic phase was separated, washed with water and brine before drying over anhydrous magnesium sulphate. The solvent was removed under reduced pressure to leave 6-iodo-1-trimethylsilylhex-1-yne as a yellow oil (20.0 g).

Workup

  1. temperaturewas heated
  2. temperatureat reflux
  3. customAfter this time the solvent was removed in vacuo
  4. customthe residue partitioned between diethyl ether and water
  5. customThe organic phase was separated
  6. washwashed with water and brine
  7. dry with materialbefore drying over anhydrous magnesium sulphate
  8. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-a022c1d44b674bacaf3d6ab58209792b
Source dataset
uspto-grants-1991_06
Patent number
US05026874

Reaction notes

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