Reaktion #2301503

Reaktionsgleichung

1-bromo-4-(trans-4-propylcyclohexyl)benzene

sodium carbonate

(R)-2-phenyl-1-(4-chlorophenyl)propane

magnesium

trimethoxyboron

hydrochloric acid

ethyl bromide

→

(R)-1-[4-[4-(trans-4-propylcyclohexyl)phenyl]phenyl]-2-phenylpropane

Lösungsmittel

tetrahydrofuran

1,2-dimethoxyethane

tetrahydrofuran

tetrahydrofuran

toluene

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONwas dropwise added
2. 2
   workup.STIRRINGby stirring for 6 hours
3. 3
   Temperaturunder reflux
4. 4
   TemperaturAfter the mixture was cooled to room temperature
5. 5
   SonstigeThe above reaction liquid
6. 6
   workup.ADDITIONwas dropwise added to a solution
7. 7
   workup.STIRRINGby stirring for 1 hour
8. 8
   TemperaturThe temperature was raised to 0° C.
9. 9
   workup.STIRRINGby stirring for 1 hour at the same temperature
10. 10
    ExtraktionAfter extraction with toluene
11. 11
    Sonstigefrom the reaction liquid
12. 12
    Waschenwashing with water
13. 13
    Sonstigedrying
14. 14
    workup.DISTILLATIONto distill off the solvent
15. 15
    workup.STIRRINGby stirring for 3 hours
16. 16
    Temperaturunder reflux
17. 17
    TemperaturThe mixture was cooled to room temperature
18. 18
    Sonstigefor liquid separation
19. 19
    Waschenthe obtained organic layer was washed with water
20. 20
    Sonstigedried
21. 21
    workup.DISTILLATIONthe solvent was distilled off
22. 22
    Sonstigerecrystallization and purification by silica gel column chromatography
23. 23
    Sonstigeto obtain 240 g of aimed (R)-1-[4-[4-(trans-4-propylcyclohexyl)phenyl]phenyl]-2-pheynylpropane
24. 24
    Sonstige130.8° C., MS m/e

Vorschrift

70 ml of tetrahydrofuran was added to 25.3 g (1.04 mol) of magnesium, and a solution having 9.45 g (0.087 mol) of ethyl bromide and 200 g (0.867 mol) of (R)-2-phenyl-1-(4-chlorophenyl)propane dissolved in 250 ml of tetrahydrofuran was dropwise added thereto over a period of 30 minutes at room temperature with stirring, followed by stirring for 6 hours under reflux. After the mixture was cooled to room temperature, 650 ml of tetrahydrofuran was added thereto. The above reaction liquid was dropwise added to a solution having 112 g (0.44 mol) of trimethoxyboron dissolved in 300 ml of tetrahydrofuran over a period of 1 hour at −20° C., followed by stirring for 1 hour. The temperature was raised to 0° C., 700 ml of 3M hydrochloric acid was dropwise added, followed by stirring for 1 hour at the same temperature. After extraction with toluene from the reaction liquid, washing with water and drying were carried out to distill off the solvent. To a 1,2-dimethoxyethane 800 ml solution of the obtained residue and 238 g (0.845 mol) of 1-bromo-4-(trans-4-propylcyclohexyl)benzene, 1160 ml of an aqueous solution of 19.5 g (16.9 mmol) of tetrakistriphenylphosphine palladium and 260 g (2.45 mol) of sodium carbonate was added, followed by stirring for 3 hours under reflux. The mixture was cooled to room temperature, toluene was added thereto for liquid separation, and the obtained organic layer was washed with water and dried, the solvent was distilled off, and recrystallization and purification by silica gel column chromatography were carried out to obtain 240 g of aimed (R)-1-[4-[4-(trans-4-propylcyclohexyl)phenyl]phenyl]-2-pheynylpropane. Melting point: 93.8° C., TSI: 130.8° C., MS m/e: 396 (M+)

Quelle