Triphenyl phosphite → 4-(4-propylcyclohexyl)cyclohexyl-2Z-butene

Into a flask, were placed triphenylphosphite (2.6 g, 10 mmol) and 4-bromophenethylbromide (2.6 g, 10 mmol) prepared from 4-bromophenethylalcohol, followed by adding and dissolving xylene (10 ml), heating under reflex for 10 hours after the completion of reaction, filtering off the deposited white crystals of 4-bromo-phenethyltriphenylphosphoniumbromide, and drying the white crystals (5.1 g, 9.5 mmol). The obtained white crystals were dissolved into THF (30 ml), followed by stirring under ice cooling, adding potassium-t-butoxid (1 g, 9 mmol) slowly into the reaction solution, stirring the solution at room temperature for 2 hours after the completion of dropping, adding THF (20 ml) solution of 4-(4-propylcyclohexyl)cyclohexylacetaldehyde (2.2 g, 9 mmol), further stirring for 5 hours, adding ether after the completion of reaction, filtrating off white solid deposited, concentrating the filtrate under reduced pressure, purifying the obtained brown oil by means of silica gel chromatography, to obtain a mixture (2.2 g, 5.3 mmol) of 1-(4-bromophenyl)-4-(4-(4-propylcyclohexyl)cyclohexyl-2Z-butene with its E-isomer.

1. customInto a flask, were placed
2. additionby adding
3. temperatureheating under reflex for 10 hours
4. customafter the completion of reaction
5. filtrationfiltering off the deposited white crystals of 4-bromo-phenethyltriphenylphosphoniumbromide
6. stirringstirring the solution at room temperature for 2 hours after the completion
7. stirringfurther stirring for 5 hours
8. customafter the completion of reaction
9. filtrationfiltrating off white solid
10. concentrationconcentrating the filtrate under reduced pressure
11. custompurifying the obtained brown oil by means of silica gel chromatography

ORD record

ord-e4307dd4f8f346b5a67e209a2bb018e2

Source dataset

uspto-grants-1995_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05401434