Sodium Iodide → HCID 12016346, compound

HRID 2297705Notes

Reaction equation

HRID 2297705 reaction equation
[I-].[Na+].[CH3:3][O:4][CH2:5][CH2:6][NH2:7].[O:8]([CH2:16][CH2:17]Br)[Si:9]([C:12]([CH3:15])([CH3:14])[CH3:13])([CH3:11])[CH3:10]>C(O)C>[O:8]([CH2:16][CH2:17][NH:7][CH2:6][CH2:5][O:4][CH3:3])[Si:9]([C:12]([CH3:15])([CH3:14])[CH3:13])([CH3:11])[CH3:10]

Participants

5

Reactant 3

HCID 5238Sodium IodideHCID 80182-MethoxyethylamineHCID 3608067(2-Bromoethoxy)-tert-butyldimethylsilane

Product 1

HCID 12016346HCID 12016346, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Sodium iodide (14.48 g) is added to a solution of 2-methoxyethylamine (14 ml) and 2-(t-butyldimethylsiloxy)ethyl bromide (7.00 g) in ethanol (65 ml), and the mixture is refluxed overnight with stirring. The reaction mixture is concentrated under reduced pressure, water is added to the residue, and the whole is extracted with chloroform. The organic layer is washed with saturated brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The resulting residue is purified by silica gel column chromatography to give 4.13 g (55%) of the titled compound (Reference compound No. 14-1).

Workup

  1. temperaturethe mixture is refluxed overnight
  2. concentrationThe reaction mixture is concentrated under reduced pressure, water
  3. additionis added to the residue
  4. extractionthe whole is extracted with chloroform
  5. washThe organic layer is washed with saturated brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe resulting residue is purified by silica gel column chromatography

Sources & evidence

ORD record
ord-a4e86e9ebcff4525a1b5d3f41ce0d1f7
Source dataset
uspto-grants-2002_12
Patent number
US06492370B1

Reaction notes

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