Potassium tert-butoxide → 1-[2-(4-Pentyl-cyclohexyl)ethenyl]-4-(4-vinylcyclohexyl)benzene

HRID 1893073Notes

Reaction equation

HRID 1893073 reaction equation
[CH3:1]C(C)([O-])C.[K+].[CH2:7]([CH:12]1[CH2:17][CH2:16][CH:15]([CH:18]=[CH:19][C:20]2[CH:25]=[CH:24][C:23]([C@H:26]3[CH2:31][CH2:30][C@H:29]([CH:32]=O)[CH2:28][CH2:27]3)=[CH:22][CH:21]=2)[CH2:14][CH2:13]1)[CH2:8][CH2:9][CH2:10][CH3:11]>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C1COCC1>[CH2:7]([CH:12]1[CH2:17][CH2:16][CH:15]([CH:18]=[CH:19][C:20]2[CH:25]=[CH:24][C:23]([CH:26]3[CH2:31][CH2:30][CH:29]([CH:32]=[CH2:1])[CH2:28][CH2:27]3)=[CH:22][CH:21]=2)[CH2:14][CH2:13]1)[CH2:8][CH2:9][CH2:10][CH3:11]

Participants

5

Reactant 2

HCID 23665647Potassium tert-butoxideHCID 178442116HCID 178442116, compound

Product 1

HCID 584532211-[2-(4-Pentyl-cyclohexyl)ethenyl]-4-(4-vinylcyclohexyl)benzene

Reagents, catalysts & solvents 2

HCID 74505Methyltriphenyliphosphonium bromideCatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

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.

Workup

  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 white precipitate was filtered under reduced pressure
  4. washthe filtrate was washed by water (100 ml)
  5. extractionextracted with ether (20 ml×1 time) The aqueous layer
  6. extractionwas extracted by chloroform (20 ml×3 times)
  7. customThe organic layer was collected
  8. washwashed by water (30 ml×2 times) and salt water (brine, 20 ml×1 time)
  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. dissolutionThe remnant was dissolved in chloroform (3 ml)
  13. additioncold ethanol (8 ml) was added dropwise by pipette
  14. stirringstirred with glass rod
  15. customto recrystallize 1.02 g (77%) of 1-[2-(4-pentyl-cyclohexyl)ethenyl]-4-(4-vinyl-cyclohexyl)benzene

Sources & evidence

ORD record
ord-0a6ddf23cec643a88a3f706648ea5e27
Source dataset
uspto-grants-2013_08
Patent number
US08512598B2

Reaction notes

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