Reacción #2344606

Ecuación de reacción

4-(3-hydroxy-3,3-dimethyl-1-propynyl)-1-bromobenzene

hydrogen peroxide

sodium hydroxide

→

4-(3-hydroxy-3,3-dimethyl-1-propynyl)-1-(1-trans-pentenyl)benzene

Rendimiento 163.5%

Disolventes

tetrahydrofuran

tetrahydrofuran

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroIn a four necked flask equipped with a stirrer, a reflux condenser
2. 2
   workup.ADDITIONwere charged
3. 3
   workup.ADDITIONwas dropwise added at room temperature
4. 4
   Temperaturaby heat
5. 5
   Temperaturarefluxing for 6 hours
6. 6
   workup.STIRRINGby stirring for 1 hour
7. 7
   ExtracciónThe mixture was extracted with toluene and water
8. 8
   LavadoThe organic layer was washed with water twice
9. 9
   Secadodried over anhydrous magnesium sulfate
10. 10
    OtroAfter removing the solvents
11. 11
    Otrothe residue was purified by silica gel column chromatography

Procedimiento

In a four necked flask equipped with a stirrer, a reflux condenser and a thermometer which had been replaced by a nitrogen atmosphere, 4-(3-hydroxy-3,3-dimethyl-1-propynyl)-1-bromobenzene (3.6 g, 15 mmol), tetrakis(triphenylphosphine)palladium (0.06 g, 0.05 mmol), sodium hydroxide (0.8 g, 20 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 removing the solvents, 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: 83%. Melting point: 65° C.

Fuente