Sodium Iodide → Silane, (5-iodo-1-pentynyl)trimethyl-

HRID 129319Notes

Reaction equation

HRID 129319 reaction equation
Cl[CH2:2][CH2:3][CH2:4][C:5]#[C:6][Si:7]([CH3:10])([CH3:9])[CH3:8].[I-:11].[Na+]>CC(=O)CC>[I:11][CH2:2][CH2:3][CH2:4][C:5]#[C:6][Si:7]([CH3:10])([CH3:9])[CH3:8]

Participants

4

Reactant 2

HCID 5238Sodium IodideHCID 27579421-Chloro-5-(trimethylsilyl)-4-pentyne

Product 1

HCID 11140046Silane, (5-iodo-1-pentynyl)trimethyl-Yield 93.8%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

A mixture of 5-chloro-1-trimethylsilylpent-1-yne (13.5 g) and sodium iodide (29 g) in butanone (100 ml) was heated at reflux 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 5-iodo-1-trimethylsilylpent-1-yne as a colourless oil (19.3 g).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 10 hours
  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-37fdbc60cac44c15b76a3d911c671799
Source dataset
uspto-grants-1995_11
Patent number
US05466710

Reaction notes

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