Sodium Iodide → HCID 54338254, compound

HRID 465701Notes

Reaction equation

HRID 465701 reaction equation
[I-].[Na+].C(N(CC)CC)C.[CH3:10][C:11]([CH3:15])=[CH:12][CH:13]=[O:14].Cl[Si:17]([CH3:20])([CH3:19])[CH3:18]>C(#N)C.CCCCC>[CH3:18][Si:17]([CH3:20])([CH3:19])[O:14][CH:13]=[CH:12][C:11]([CH3:15])=[CH2:10]

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 6397ChlorotrimethylsilaneHCID 8471TriethylamineHCID 610203-Methyl-2-butenal

Product 1

HCID 54338254HCID 54338254, compoundYield 71.8%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8003PentaneSolvent

Procedure

To a suspension of 180 g of anhydrous sodium iodide in 300 ml of dry acetonitrile is added a solution of 112 g of triethylamine and 84 g of 3-methyl-2-butenal in 400 ml of pentane at room temperature. Added dropwise to the above solution is 109 g of chlorotrimethylsilane at 35°-38° C. and the mixture stirred for 4 hours at 40°-45° C. The resulting solid is filtered, washed with 400 ml of pentane and the solvent evaporated to a residue. The residue is distilled to afford 112 g of the desired product, B.P. 56°-60° C./35 mm, nD20 1.4496.

Workup

  1. additionAdded dropwise to the above solution
  2. customat 35°-38° C.
  3. filtrationThe resulting solid is filtered
  4. washwashed with 400 ml of pentane
  5. customthe solvent evaporated to a residue
  6. distillationThe residue is distilled

Sources & evidence

ORD record
ord-01aac02eae2d427ab8670e5b545b8319
Source dataset
uspto-grants-1992_10
Patent number
US05153337

Reaction notes

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