Reaktion #1980254

Reaktionsgleichung

water

cyclohexane carboxylate

4-{4-[2-(4-pentyl-cyclohexyl)-ethenyl]-phenyl}cyclohexane carboxylic acid methyl ester

HCl

vitride

→

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

Ausbeute 55.1%

Lösungsmittel

toluene

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONwas added to another 2-neck flask
2. 2
   workup.ADDITIONwas added slowly dropwise at −70° C. for 30 minutes
3. 3
   FiltrationWhite precipitate was filtered under reduced pressure
4. 4
   Extraktionthe filtrate was extracted by toluene (20 ml×three times)
5. 5
   SonstigeThe organic layer was collected
6. 6
   Waschenwashed
7. 7
   workup.DISTILLATIONby distilled water (10 ml×two times)
8. 8
   Trocknendried with anhydrous Na2SO4
9. 9
   Einengenconcentrated under reduced pressure
10. 10
    SonstigeThe obtained residue was purified by column chromatography (hexane:ether=5:1, Rf=0.32)

Vorschrift

Vitride (3.3M in toluene, 10 eq, 26.6 ml, 87.7 mmol) was added with syringe to a flask filled with Argon gas at 0° C., and morpholine (10 eq, 7.67 ml, 87.7 mmol) was added slowly dropwise with syringe. Then, toluene (a half of morpholine mmol, 44 ml) was added dropwise with syringe to produce vitride solution. 88 ml of a solution including cyclohexane carboxylate compound (3.48 g, 8.77 mmol) obtained in Example 4-1 in toluene a solution was added to another 2-neck flask filled with argon gas, and vitride solution was added slowly dropwise at −70° C. for 30 minutes. Then, the solution was stirred with maintaining −30 to −50° C. for 6 hours and water was added very slowly dropwise to the flask. 1M HCl was slowly added to the flask to neutralize the reaction solution. White precipitate was filtered under reduced pressure and the filtrate was extracted by toluene (20 ml×three times). The organic layer was collected, washed by distilled water (10 ml×two times), dried with anhydrous Na2SO4 and concentrated under reduced pressure. The obtained residue was purified by column chromatography (hexane:ether=5:1, Rf=0.32) to produce 1.77 g (55%) of trans-4-{4-[2-(4-pentylcyclohexyl)ethenyl]phenyl}cyclohexane carbaldehyde.

Quelle