Reaktion #813630

ord-6a21a4a0a9894f28911d27993d599338

Reaktionsgleichung

CC=CCBr
1-bromo-2-butene
CCC[C@H]1CC[C@H]([C@H]2CC[C@H]([C@H]3CC[C@H](O)CC3)CC2)CC1
trans-4-(trans-4-(trans-4-propylcyclohexyl)cyclohexyl)cyclohexanol
[H-].[Na+]
NaH
→
CC=CCO[C@H]1CC[C@H]([C@H]2CC[C@H]([C@H]3CC[C@H](CCC)CC3)CC2)CC1
1-(2-butenyloxy)-trans-4-(trans-4-(trans-4-propylcyclohexyl)cyclohexyl)cyclohexane
Ausbeute 49.9%

Edukte

—
ice water
CC=CCBr
1-bromo-2-butene
CCC[C@H]1CC[C@H]([C@H]2CC[C@H]([C@H]3CC[C@H](O)CC3)CC2)CC1
trans-4-(trans-4-(trans-4-propylcyclohexyl)cyclohexyl)cyclohexanol
[H-].[Na+]
NaH

Reagenzien

Keine

Lösungsmittel

CN(C)C=O
DMF
CN(C)C=O
DMF
CN(C)C=O
DMF

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    workup.ADDITIONAfter completion of the dropwise addition
  2. 2
    workup.STIRRINGthe reaction mixture was stirred for 2 hours
  3. 3
    Sonstigeto rise up to about 80° C.
  4. 4
    workup.ADDITIONAfter completion of the dropwise addition
  5. 5
    Temperaturthe mixture was heated
  6. 6
    Temperaturunder reflux at the same temperature for 5 hours
  7. 7
    Temperaturto cool down to room temperature
  8. 8
    Extraktionextracted with 500 ml of toluene
  9. 9
    WaschenThe organic layer was washed three times with water
  10. 10
    Trocknendried over anhydrous magnesium sulfate
  11. 11
    workup.DISTILLATIONthe solvent was distilled off under reduced pressure

Vorschrift

To a solution of 10.0 g (33.1 mmol) of trans-4-(trans-4-(trans-4-propylcyclohexyl)cyclohexyl)cyclohexanol in 100 ml of DMF was added dropwise, while stirring the solution at room temperature, a suspension of 1.19 g (49.6 mmol) of NaH in 10 ml of DMF. After completion of the dropwise addition, the reaction mixture was stirred for 2 hours and then the temperature of the reaction mixture was gradually allowed to rise up to about 80° C. and a solution of 5.35 g (39.7 mmol) of 1-bromo-2-butene in 20 ml of DMF was added dropwise. After completion of the dropwise addition, the mixture was heated under reflux at the same temperature for 5 hours. After the reaction solution was allowed to cool down to room temperature, the reaction product was poured into an ice-water and extracted with 500 ml of toluene. The organic layer was washed three times with water, dried over anhydrous magnesium sulfate and the solvent was distilled off under reduced pressure. A silica gel column chromatography (developing solvent: toluene) of the residue gave 5.96 g of crude 1-(2-butenyloxy)-trans-4-(trans-4-(trans-4-propylcyclohexyl)cyclohexyl)cyclohexane.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US05709820uspto-grants-1998_01