Hydrochloric Acid → Allyl-(4-ethynyl-phenyl)-dimethyl silane
Reaction equation
[CH2:1]([Si:4]([CH3:18])([CH3:17])[C:5]1[CH:10]=[CH:9][C:8]([C:11]#[C:12][Si](C)(C)C)=[CH:7][CH:6]=1)[CH:2]=[CH2:3].[OH-].[K+].Cl>CO>[CH2:1]([Si:4]([C:5]1[CH:10]=[CH:9][C:8]([C:11]#[CH:12])=[CH:7][CH:6]=1)([CH3:18])[CH3:17])[CH:2]=[CH2:3]Participants
Procedure
1.36 g (5 mmol) of 1-(allyldimethylsilanyl)-4-trimethylsilanylethynyl benzene was suspended in 5 mL of methanol and 5 mL of methanol solution containing 330 mg (5 mmol) of potassium hydroxide was added to the resultant suspension at a temperature of 0° C. and stirred for 40 minutes. Further, the resultant solution was turned acidic by adding 5 mL of 1M hydrochloric acid thereto and subjected to extraction using ether. The organic layer thus created was then washed with saturated sodium hydrogen carbonate and also with saturated brine and dried using magnesium sulfate as a desiccating agent. After the desiccating agent was removed by filtration, the solvent was removed a rotary evaporator to obtain a crude product, which was then purified by silica gel column chromatography (developing solvent: hexane) to obtain 0.90 g (4.49 mmol) of allyl-(4-ethynyl-phenyl)-dimethyl silane (3a), which was colorless and oily. The yield was 90%.
Workup
- extractionsubjected to extraction
- washThe organic layer thus created was then washed with saturated sodium hydrogen carbonate and also with saturated brine
- customdried
- customAfter the desiccating agent was removed by filtration
- customthe solvent was removed
- customa rotary evaporator
- customto obtain a crude product, which
- customwas then purified by silica gel column chromatography (developing solvent: hexane)
Sources & evidence
- ORD record
- ord-185d21ad3fda475c86e7d4a114b15204
- Source dataset
- uspto-grants-2007_08
- Patent number
- US07253243B2
Reaction notes
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