Ammonium Chloride → 1-(Allyldimethylsilanyl)-4-trimethylsilanylethynyl benzene

HRID 852976

Reaction equation

HRID 852976 reaction equation
C([Li])CCC.Br[C:7]1[CH:12]=[CH:11][C:10]([C:13]#[C:14][Si:15]([CH3:18])([CH3:17])[CH3:16])=[CH:9][CH:8]=1.[CH2:19]([Si:22](Cl)([CH3:24])[CH3:23])[CH:20]=[CH2:21].[Cl-].[NH4+]>C1COCC1.CCCCCC>[CH2:19]([Si:22]([CH3:24])([CH3:23])[C:7]1[CH:12]=[CH:11][C:10]([C:13]#[C:14][Si:15]([CH3:18])([CH3:17])[CH3:16])=[CH:9][CH:8]=1)[CH:20]=[CH2:21]

Participants

7

Reactant 4

HCID 25517Ammonium ChlorideHCID 77646AllylchlorodimethylsilaneHCID 4226980(4-Bromophenylethynyl)trimethylsilaneHCID 178418339Butyllithium

Product 1

HCID 121840521-(Allyldimethylsilanyl)-4-trimethylsilanylethynyl benzeneYield 93.3%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Procedure

6.4 mL (10 mmol) of a 1.6 M hexane solution of butyl lithium was added to 60 mL of THF solution containing 2.54 g (10 mmol) of (4-bromo-phenylethynyl)trimethyl silane under an argon atmosphere at a temperature of −78° C. and the resultant mixture was stirred for 30 minutes. Then, 1.5 mL (10 mmol) of allylchlorodimethyl silane was added to the mixture and stirred for 10 minutes, after which the temperature of the mixture was gradually returned to room temperature and additionally stirred for two hours. After an aqueous solution of ammonium chloride was added to the mixture, the resultant solution was subjected to extraction using ether. The organic layer thus created was then washed with saturated brine and dried using magnesium sulfate as a desiccating agent. After the desiccating agent was removed by filtration, the solvent was removed by a rotary evaporator to obtain a crude product, which was then purified by silica gel column chromatography (developing solvent: hexane) to obtain 2.54 g (9.33 mmol) of 1-(allyldimethylsilanyl)-4-trimethylsilanylethynyl benzene. The yield was 93%.

Workup

  1. customwas gradually returned to room temperature
  2. stirringadditionally stirred for two hours
  3. extractionthe resultant solution was subjected to extraction
  4. washThe organic layer thus created was then washed with saturated brine
  5. customdried
  6. customAfter the desiccating agent was removed by filtration
  7. customthe solvent was removed by a rotary evaporator
  8. customto obtain a crude product, which
  9. customwas then purified by silica gel column chromatography (developing solvent: hexane)

Sources & evidence

ORD record
ord-e2bf638c0ba840c7b69d7cc6a8a7b726
Source dataset
uspto-grants-2007_08
Patent number
US07253243B2

Linked notes

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