Reaktion #1980255

Reaktionsgleichung

trans-4-{4-[2-(4-pentyl-cyclohexyl)ethenyl]phenyl}cyclohexane carbaldehyde

trans-4-{4-[2-(4-pentylcyclohexyl)ethenyl]phenyl}cyclohexane carbaldehyde

Potassium tert-butoxide

→

1-[2-(4-pentyl-cyclohexyl)ethenyl]-4-(4-vinylcyclohexyl)benzene

Lösungsmittel

THF

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGThen, the solution was stirred for 30 minutes at a room temperature
2. 2
   workup.STIRRINGwas stirred at a room temperature for 24 hours
3. 3
   FiltrationThe white precipitate was filtered under reduced pressure
4. 4
   Waschenthe filtrate was washed by water (100 ml)
5. 5
   Extraktionextracted with ether (20 ml×1 time) The aqueous layer
6. 6
   Extraktionwas extracted by chloroform (20 ml×3 times)
7. 7
   SonstigeThe organic layer was collected
8. 8
   Waschenwashed by water (30 ml×2 times) and salt water (brine, 20 ml×1 time)
9. 9
   Trocknendried by anhydrous Na2SO4
10. 10
    Einengenconcentrated under reduced pressure
11. 11
    SonstigeThe obtained residue was purified by column chromatography (silica gel, hexane, Rf=0.36)
12. 12
    workup.DISSOLUTIONThe remnant was dissolved in chloroform (3 ml)
13. 13
    workup.ADDITIONcold ethanol (8 ml) was added dropwise by pipette
14. 14
    workup.STIRRINGstirred with glass rod
15. 15
    Sonstigeto recrystallize 1.02 g (77%) of 1-[2-(4-pentyl-cyclohexyl)ethenyl]-4-(4-vinyl-cyclohexyl)benzene

Vorschrift

Potassium tert-butoxide (1.0 eq, 0.44 g, 3.62 mmol) was added slowly with stirring for 3 minutes to 32 ml of solution including methyltriphenylphosphonium bromide (1.2 eq, 1.55 g, 4.33 mmol) dissolved in THF. Then, the solution was stirred for 30 minutes at a room temperature and THF solution (35 ml) of trans-4-{4-[2-(4-pentyl-cyclohexyl)ethenyl]phenyl}cyclohexane carbaldehyde (1.32 g, 3.62 mmol) obtained in Example 4-2 was added slowly dropwise for 10 minutes to reaction mixture, and then was stirred at a room temperature for 24 hours. The white precipitate was filtered under reduced pressure and the filtrate was washed by water (100 ml) and extracted with ether (20 ml×1 time) The aqueous layer was extracted by chloroform (20 ml×3 times). The organic layer was collected, washed by water (30 ml×2 times) and salt water (brine, 20 ml×1 time), dried by anhydrous Na2SO4 and concentrated under reduced pressure. The obtained residue was purified by column chromatography (silica gel, hexane, Rf=0.36). The remnant was dissolved in chloroform (3 ml), and cold ethanol (8 ml) was added dropwise by pipette and stirred with glass rod to recrystallize 1.02 g (77%) of 1-[2-(4-pentyl-cyclohexyl)ethenyl]-4-(4-vinyl-cyclohexyl)benzene.

Quelle