Potassium tert-butoxide → 1-[2-(4-Propylcyclohexyl)ethyl]-4-(4-vinylcyclohexyl)benzene

Potassium tert-butoxide (0.86 g, 7.01 mmol) was added slowly with stirring for 3 minutes to 32 ml of solution including methyltriphenylphosphonium bromide (3 g, 8.41 mmol) dissolved in THF. Then, the solution was stirred for 30 minutes at a room temperature and THF solution (25 ml) of 4-{4-[2-(4-propyl-cyclohexyl)ethyl]phenyl}cyclohexane carbaldehyde (2.39 g, 7.01 mmol) was added slowly dropwise to reaction mixture, and then was stirred at a room temperature for 24 hours. The 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 NaCl solution, dried by anhydrous Na2SO4 and concentrated under reduced pressure. The obtained residue was purified by column chromatography (silica gel, hexane, Rf=0.36) and was recrystallized by addition of chloroform and ethanol to obtain 1.9 g (80%) of 1-[2-(4-propyl-cyclohexyl)ethyl]-4-(4-vinyl-cyclohexyl)benzene.

1. stirringThen, the solution was stirred for 30 minutes at a room temperature
2. stirringwas stirred at a room temperature for 24 hours
3. filtrationThe precipitate was filtered under reduced pressure
4. washthe filtrate was washed by water (100 ml)
5. extractionextracted with ether (20 ml×1 time)
6. extractionThe aqueous layer was extracted by chloroform (20 ml×3 times)
7. customThe organic layer was collected
8. washwashed by NaCl solution
9. dry with materialdried by anhydrous Na2SO4
10. concentrationconcentrated under reduced pressure
11. customThe obtained residue was purified by column chromatography (silica gel, hexane, Rf=0.36)
12. customwas recrystallized by addition of chloroform and ethanol

ORD record

ord-06e3285655524a18910a0867f4598c00

Source dataset

uspto-grants-2013_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08512598B2