Sodium Iodide → Diethoxy(iodomethyl)phenylsilane

HRID 2413315Notes

Reaction equation

HRID 2413315 reaction equation
Cl[CH2:2][Si:3]([O:13][CH2:14][CH3:15])([O:10][CH2:11][CH3:12])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[I-:16].[Na+].[Cl-].C(C([NH3+])(C(=O)CCCCCCC)C(=O)CCCCCCC)(=O)CCCCCCC>C(O)C>[CH2:11]([O:10][Si:3]([O:13][CH2:14][CH3:15])([CH2:2][I:16])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)[CH3:12]

Participants

5

Reactant 3

HCID 5238Sodium IodideHCID 20401749Chloromethyl(diethoxy)phenylsilaneHCID 77620884Tricaprylylmethyl ammonium chloride

Product 1

HCID 13474598Diethoxy(iodomethyl)phenylsilaneYield 50%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 12.8 g (0.052 mol) of chloromethyl(diethoxy)phenylsilane, 9.4 g (0.062 mol) of sodium iodide and 0.21 g (0.52 mol) of tricaprylylmethylammonium chloride (Aliquat® 336) in 10 ml of ethyl alcohol was refluxed for 12 hours, cooled, filtered, and evaporated. The filtrate was diluted with water and extracted with ether. The ether solution was washed with brine, dried over magnesium sulfate, evaporated, and distilled to provide 8.7 g (50%) of the title compound as a clear liquid: b.p. 86°-100° (0.15 mm); nD19 1.5204; ir (neat) 2980, 1590, 1480, 1430, 1390, 1290, 1165 cm-1 ; nmr (CDCl3) 1.25 (6H, t, J=7) and 7.3-7.9 (5H, m).

Workup

  1. temperaturewas refluxed for 12 hours
  2. temperaturecooled
  3. filtrationfiltered
  4. customevaporated
  5. additionThe filtrate was diluted with water
  6. extractionextracted with ether
  7. washThe ether solution was washed with brine
  8. dry with materialdried over magnesium sulfate
  9. customevaporated
  10. distillationdistilled

Sources & evidence

ORD record
ord-267ba5363ddb48f282dce4c1347785e3
Source dataset
uspto-grants-1985_01
Patent number
US04496551

Reaction notes

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