Iodine → Trimethyl-(4-prop-1-en-2-ylphenyl)silane

HRID 1034460

Reaction equation

HRID 1034460 reaction equation
[Mg].ClC1C=CC(C=CC)=CC=1.II.Cl[C:15]1[CH:23]=[CH:22][C:18]([C:19]([CH3:21])=[CH2:20])=[CH:17][CH:16]=1.Cl[Si:25]([CH3:28])([CH3:27])[CH3:26]>C1COCC1.O>[CH3:26][Si:25]([CH3:28])([CH3:27])[C:15]1[CH:23]=[CH:22][C:18]([C:19]([CH3:21])=[CH2:20])=[CH:17][CH:16]=1

Participants

8

Reactant 5

HCID 807IodineHCID 6397ChlorotrimethylsilaneHCID 743814-Chloro-alpha-methylstyreneHCID 5462224Magnesium2×HCID 534265131-Chloro-4-(prop-1-en-1-yl)benzene

Product 1

HCID 325452Trimethyl-(4-prop-1-en-2-ylphenyl)silane

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent3×

Conditions

Temperature
40 °C

Procedure

Placing 2 g (83 mmol) of dry magnesium into a 250 mL flask equipped with a condenser, a dropping funnel and a magnetic stirrer, the reaction was carried out in a nitrogen atmosphere. The magnesium was initially activated by adding 1 mL of p-chloro-methylstyrene (Aldrich, Germany) with 0.5 g iodine in 5 mL THF at 50° C. for a period of 30 minutes. Into the mixture a solution of 11 g (72 mmol) of p-chloro-α-methylstyrene in 50 mL THF was dropped over a period of 12 hours under reflux. The reaction mixture was cooled to 40° C., then 7.8 g (72 mmol) of chlorotrimethylsilane (Fluka, Japan) in 30 mL of THF were added dropwise and reacted for 24 hours. After the reaction was completed, a large amount of water was added and the reaction mixture was extracted with ether. The ether layer was dried over magnesium sulfate, and distilled under reduced pressure, bp 66°-67° C./2 mmHg. Yield, 56%. The colorless liquid crude product was purified by column chromatography, which was performed on silica gel using n-hexane as an eluent. The product was identified by IR and 1H-NMR spectroscopy.

Workup

  1. customequipped with a condenser, a dropping funnel and a magnetic stirrer
  2. temperatureunder reflux
  3. customreacted for 24 hours
  4. extractionthe reaction mixture was extracted with ether
  5. dry with materialThe ether layer was dried over magnesium sulfate
  6. distillationdistilled under reduced pressure, bp 66°-67° C./2 mmHg
  7. customYield
  8. customThe colorless liquid crude product was purified by column chromatography, which

Sources & evidence

ORD record
ord-120483f56eb1460ea11663fe15a91260
Source dataset
uspto-grants-1994_05
Patent number
US05317069

Linked notes

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