Hydrogen Peroxide → HCID 22922863, compound

HRID 2257429Notes

Reaction equation

HRID 2257429 reaction equation
[CH2:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]#[C:11][C:12]2[CH:17]=[CH:16][C:15](OS(C(F)(F)F)(=O)=O)=[CH:14][CH:13]=2)=[CH:6][CH:5]=1)[CH2:2][CH3:3].[OH-].[Na+].CN1[CH2:34][CH2:33]NCC1.OO.O1C[CH2:40][CH2:39][CH2:38]1>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH2:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]#[C:11][C:12]2[CH:17]=[CH:16][C:15](/[CH:38]=[CH:39]/[CH2:40][CH2:33][CH3:34])=[CH:14][CH:13]=2)=[CH:6][CH:5]=1)[CH2:2][CH3:3]

Participants

7

Reactant 5

HCID 784Hydrogen PeroxideHCID 8028Tetrahydrofuran2×HCID 14798Sodium Hydroxide2×HCID 531671-MethylpiperazineHCID 22922905HCID 22922905, compound

Product 1

HCID 22922863HCID 22922863, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 178418397HCID 178418397, compoundCatalyst

Procedure

In a four necked flask equipped with a stirrer, a reflux condenser and a thermometer which had been replaced by a nitrogen atmosphere, 1-(4-propylphenyl)-2-(4-trifluoromethanesulfonyloxyphenyl)acetylene (4.4 g, 12 mmol), tetrakis(triphenylphosphine)palladium (0.23 g, 0.2 mmol), sodium hydroxide (2.4 g, 60 mmol), tetrahydrofuran (40 ml) and N-methylpiperazine (10 ml) were charged. Then, to the mixture, a solution of E-1-pentenylcatecholborane (20 mmol) in tetrahydrofuran (50 ml) was dropwise added at room temperature, followed by heat refluxing for 6 hours while stirring. After cooling the reaction mixture to room temperature, 10% aqueous solution of sodium hydroxide (5 ml) and 30% aqueous hydrogen peroxide (2 ml) were added to the mixture, followed by stirring for 1 hour. The mixture was extracted with ethyl ether. The organic layer was washed with saturated aqueous solution of sodium chloride (20 ml each) twice and dried over anhydrous magnesium sulfate. After evaporating the solvent off, the residue was purified by silica gel column chromatography to obtain 1-(4-propylphenyl)-2-[4-(1-trans-pentenyl)phenyl]acetylene (3.0 g). Yield: 88%.

Workup

  1. customIn a four necked flask equipped with a stirrer, a reflux condenser
  2. additionwere charged
  3. temperatureby heat
  4. temperaturerefluxing for 6 hours
  5. stirringby stirring for 1 hour
  6. extractionThe mixture was extracted with ethyl ether
  7. washThe organic layer was washed with saturated aqueous solution of sodium chloride (20 ml each) twice
  8. dry with materialdried over anhydrous magnesium sulfate
  9. customAfter evaporating the solvent off, the residue
  10. customwas purified by silica gel column chromatography

Sources & evidence

ORD record
ord-48f6dd23c8e0459ab9796bdb5d737a82
Source dataset
uspto-grants-1997_08
Patent number
US05658489

Reaction notes

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