Methanol → 1-allyl-2-(4-ethynyl-phenyl)-1,1,2,2-tetramethyl-disilane

HRID 852978Notes

Reaction equation

HRID 852978 reaction equation
CO.[OH-].[K+].[CH2:5]([Si:8]([CH3:25])([CH3:24])[Si:9]([CH3:23])([CH3:22])[C:10]1[CH:15]=[CH:14][C:13]([C:16]#[C:17][Si](C)(C)C)=[CH:12][CH:11]=1)[CH:6]=[CH2:7]>Cl>[CH2:5]([Si:8]([CH3:24])([CH3:25])[Si:9]([C:10]1[CH:15]=[CH:14][C:13]([C:16]#[CH:17])=[CH:12][CH:11]=1)([CH3:23])[CH3:22])[CH:6]=[CH2:7]

Participants

5

Reactant 3

HCID 887Methanol2×HCID 14797Potassium HydroxideHCID 12184054HCID 12184054, compound

Product 1

HCID 121840551-allyl-2-(4-ethynyl-phenyl)-1,1,2,2-tetramethyl-disilaneYield 65%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Conditions

Temperature
0 °C

Procedure

45 mL of methanol containing 1.98 g (30 mmol) of potassium hydroxide was added to 45 mL of methanol containing 9.92 g (30 mmol) of 1-allyl-1,1,2,2-tetramethyl-2-(4-trimethylsilanylethynylphenyl) disilane to obtain a mixture, which was stirred for 30 minutes at a temperature of 0° C. Further, the resultant solution was turned acidic by adding 30 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 by a rotary evaporator to obtain a crude product, which was then purified by silica gel column chromatography (developing solvent: hexane) to obtain 5.03 g (19.44 mmol) of 1-allyl-2-(4-ethynyl-phenyl)-1,1,2,2-tetramethyl-disilane (4a) which was colorless and oily. The yield was 65%.

Workup

  1. customto obtain a mixture, which
  2. extractionsubjected to extraction
  3. washThe organic layer thus created was then washed with saturated sodium hydrogen carbonate and also with saturated brine
  4. customdried
  5. customAfter the desiccating agent was removed by filtration
  6. customthe solvent was removed by a rotary evaporator
  7. customto obtain a crude product, which
  8. customwas then purified by silica gel column chromatography (developing solvent: hexane)

Sources & evidence

ORD record
ord-a8902f30c57c4a8e9913fe1a45c98ffc
Source dataset
uspto-grants-2007_08
Patent number
US07253243B2

Reaction notes

Loading…