Hydrogen Peroxide → HCID 10878923, compound

In a four necked flask equipped with a stirrer, a reflux condenser and a thermometer which had been replaced by a nitrogen atmosphere, 4-(3-hydroxy-3,3-dimethyl-1-propynyl)-1- trifluoromethanesulfonyloxybenzene (3.6 g, 15 mmol), tetrakis(triphenylphosphine)palladium (0.06 g, 0.05 mmol), sodium hydroxide (1.2 g, 30 mmol) and tetrahydrofuran (60 ml) were charged. Then, to the mixture, a solution of E-1-pentenylcatecholborane prepared in Reference Example 1 (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, 30% aqueous hydrogen peroxide (2 ml) was added to the mixture, followed by stirring for 1 hour. The mixture was extracted with toluene and water. The organic layer was washed with water twice and dried over anhydrous magnesium sulfate. After evaporating the solvent off, the residue was purified by silica gel column chromatography to obtain 4-(3-hydroxy-3,3-dimethyl-1-propynyl)-1-(1-trans-pentenyl)benzene (2.8 g). Yield: 82%.

1. customIn a four necked flask equipped with a stirrer, a reflux condenser
2. additionwere charged
3. additionwas dropwise added at room temperature
4. temperatureby heat
5. temperaturerefluxing for 6 hours
6. stirringby stirring for 1 hour
7. extractionThe mixture was extracted with toluene and water
8. washThe organic layer was washed with water twice
9. dry with materialdried over anhydrous magnesium sulfate
10. customAfter evaporating the solvent off, the residue
11. customwas purified by silica gel column chromatography

ORD record

ord-2cc1ca02c85444a0a529cf5ebc96eeeb

Source dataset

uspto-grants-1997_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05658489