Sodium Iodide → HCID 53670473, compound

HRID 1196146Notes

Reaction equation

HRID 1196146 reaction equation
[Br:1][C:2](=[CH:5][CH3:6])[CH:3]=[O:4].C(N(CC)CC)C.Cl[Si:15]([CH3:18])([CH3:17])[CH3:16].[I-].[Na+]>C(#N)C.C(OCC)C>[Br:1][C:2]([CH:5]=[CH2:6])=[CH:3][O:4][Si:15]([CH3:18])([CH3:17])[CH3:16]

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 6397ChlorotrimethylsilaneHCID 8471TriethylamineHCID 322612-Bromo-2-butenal

Product 1

HCID 53670473HCID 53670473, compoundYield 85%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6342AcetonitrileSolvent

Procedure

Furthermore, 2.98 g (20 mmoles) of 2-bromobut-2-enal and 3 g (30 mmoles) of triethylamine are introduced into a 250 ml container. At room temperature, in a nitrogen atmosphere with agitation, there is added 1.63 g (30 mmoles) of chlorotrimethylsilane followed, drop by drop, by the solution of sodium iodide in acetonitrile which was previously prepared. After reaction for 90 minutes, 60 cc of anhydrous petroleum ether (petroleum ether 40-60) are added and agitation is effected for 30 minutes. The precipitate which forms is filtered off under a nitrogen atmosphere and then washed twice with 30 ml of anhydrous petroleum ether. The upper phase of the filtrate (petroleum ether) is collected and the lower phase (acetonitrile) extracted 3 times with, in each case, 30 ml of petroleum ether. The petroleum ether fractions are collected and 5 g of anhydrous magnesium sulfate added thereto. Filtration is effected over fritted glass and the solvent eliminated by vacuum distillation (rotary evaporator) in an inert atmosphere. The residue obtained is diluted in 80 cc of anhydrous ethyl ether; the precipitate is filtered and the solvent evaporated under an atmosphere of nitrogen. 3.76 g of product are obtained, representing a yield of 85%. Purity (GC) of the product obtained is 98% and its structure is confirmed by nuclear magnetic resonance and mass spectrometry.

Workup

  1. customAfter reaction for 90 minutes
  2. filtrationThe precipitate which forms is filtered off under a nitrogen atmosphere
  3. washwashed twice with 30 ml of anhydrous petroleum ether
  4. customThe upper phase of the filtrate (petroleum ether) is collected
  5. extractionthe lower phase (acetonitrile) extracted 3 times with, in each case, 30 ml of petroleum ether
  6. customThe petroleum ether fractions are collected
  7. addition5 g of anhydrous magnesium sulfate added
  8. filtrationFiltration
  9. distillationthe solvent eliminated by vacuum distillation (rotary evaporator) in an inert atmosphere
  10. customThe residue obtained
  11. filtrationthe precipitate is filtered
  12. customthe solvent evaporated under an atmosphere of nitrogen

Sources & evidence

ORD record
ord-9ed3411984ac4ee8b692d8e57b32929e
Source dataset
uspto-grants-1992_05
Patent number
US05113007

Reaction notes

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