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

HRID 1893082Notes

Reaction equation

HRID 1893082 reaction equation
[CH3:1]C(C)([O-])C.[K+].[CH2:7]([CH:10]1[CH2:15][CH2:14][CH:13]([CH2:16][CH2:17][C:18]2[CH:23]=[CH:22][C:21]([C@H:24]3[CH2:29][CH2:28][C@H:27]([CH:30]=O)[CH2:26][CH2:25]3)=[CH:20][CH:19]=2)[CH2:12][CH2:11]1)[CH2:8][CH3:9]>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C1COCC1>[CH2:7]([CH:10]1[CH2:15][CH2:14][CH:13]([CH2:16][CH2:17][C:18]2[CH:23]=[CH:22][C:21]([CH:24]3[CH2:29][CH2:28][CH:27]([CH:30]=[CH2:1])[CH2:26][CH2:25]3)=[CH:20][CH:19]=2)[CH2:12][CH2:11]1)[CH2:8][CH3:9]

Participants

5

Reactant 2

HCID 23665647Potassium tert-butoxideHCID 178439008HCID 178439008, compound

Product 1

HCID 584532181-[2-(4-Propylcyclohexyl)ethyl]-4-(4-vinylcyclohexyl)benzeneYield 65%

Reagents, catalysts & solvents 2

HCID 74505Methyltriphenyliphosphonium bromideCatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

THF solution (5 ml) including methyltriphenylphosphonium bromide (0.25 g, 0.7 mmol) was slowly added by potassium tert-butoxide (0.07 g, 0.7 mmol) for 3 minutes and then stirred for 1 hour at a room temperature. The resulting solution was added slowly dropwise by THF solution (2 ml) of trans-4-{4-[2-(4-propylcyclohexyl)ethyl]phenyl}cyclohexane-carbaldehyde (0.2 g, 0.58 mmol) and stirred for 24 hours with maintaining the same temperature. After the reaction termination, white precipitate was removed by filtration. The filtered solution was extracted by ether (10 ml×3 times) and the organic layer was collected and washed by distilled water (10 ml×2 times) and salt water (10 ml×2 times). The residue was purified by column chromatography (petroleum ether) to obtain a final product of 1-[2-(4-propylcyclohexyl)ethyl]-4-(4-vinylcyclohexyl)benzene (0.12 g, 65%).

Workup

  1. stirringstirred for 24 hours
  2. temperaturewith maintaining the same temperature
  3. customAfter the reaction termination, white precipitate was removed by filtration
  4. extractionThe filtered solution was extracted by ether (10 ml×3 times)
  5. customthe organic layer was collected
  6. washwashed
  7. distillationby distilled water (10 ml×2 times) and salt water (10 ml×2 times)
  8. customThe residue was purified by column chromatography (petroleum ether)

Sources & evidence

ORD record
ord-f39176eaad67463f9ec6954e71875f5c
Source dataset
uspto-grants-2013_08
Patent number
US08512598B2

Reaction notes

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