Iodine → Silane, (3-iodopropyl)trimethyl-

HRID 1655990Notes

Reaction equation

HRID 1655990 reaction equation
[I:1]I.[Mg:3].[CH3:4][Si:5]([CH3:11])([CH3:10])[CH2:6][CH2:7][CH2:8]O.CS([O-])(=O)=O>CCOCC>[I-:1].[Mg+2:3].[I-:1].[I:1][CH2:8][CH2:7][CH2:6][Si:5]([CH3:11])([CH3:10])[CH3:4]

Participants

7

Reactant 4

HCID 807IodineHCID 762131-Propanol, 3-(trimethylsilyl)-HCID 85257MethanesulfonateHCID 5462224Magnesium

Product 2

HCID 553328Silane, (3-iodopropyl)trimethyl-HCID 5462737Magnesium diiodide

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

An ethereal solution of magnesium iodide was prepared by adding 4.85 g (19 mmol) of iodine to 0.46 g (19 mmol) of magnesium in suspension in 40 ml of dry ether. 28 ml of this solution was added to a solution containing the crude 3-(trimethylsilyl)-1-propanol, methanesulfonate in 10 ml of ether. The reaction mixture was stirred for 3 hours at room temperature and then partitioned between ether and water, the organic phase was separated and further washed with aqueous sodium thiosulfate. After evaporation of the solvent, 1.6 g of (3-iodopropyl)trimethysilane was obtained as a colorless liquid.

Workup

  1. custompartitioned between ether and water
  2. customthe organic phase was separated
  3. washfurther washed with aqueous sodium thiosulfate
  4. customAfter evaporation of the solvent

Sources & evidence

ORD record
ord-33885d17323f4cb7a2d9119f79b0c513
Source dataset
uspto-grants-1993_10
Patent number
US05252587

Reaction notes

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