Hydrogen Peroxide → HCID 22922870, compound

In a four necked flask equipped with a stirrer, a reflux condenser and a thermometer which had been replaced by a nitrogen atmosphere, 1-(4-trifluoromethylphenyl)-2-(4-bromophenyl)acetylene (3.9 g, 12 mmol), tetrakis(triphenylphosphine)palladium (0.23 g, 0.2 mmol), sodium hydroxide (2.4 g, 60 mmol) and tetrahydrofuran (60 ml) were charged. Then, to the mixture, a solution of E-1-heptenylcatecholborane (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 removing the solvent, the residue was purified by silica gel column chromatography to obtain 1-(4-trifluoromethylphenyl)-2-[4-(1-trans-pentenyl)phenyl]acetylene (3.2 g). Yield: 84%.

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 removing the solvent
10. customthe residue was purified by silica gel column chromatography

ORD record

ord-dd5d8e784cb14a59a0068ea5e90e2d90

Source dataset

uspto-grants-1997_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05658489