Reaktion #1351642

Reaktionsgleichung

trans-4-(trans-4-propylcyclohexyl)-cyclohexanecarbaldehyde

ethyl diethylphosphinoacetate

sodium hydride

hydrogen

→

ethyl 3-(trans-4-(trans-4-propylcyclohexyl)cyclohexyl)propenoate

Ausbeute 46.7%

Lösungsmittel

THF

water

THF

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeIn a flask equipped with a stirrer
2. 2
   workup.STIRRINGthe solution was further stirred for 2 hours
3. 3
   workup.ADDITIONwas added dropwise
4. 4
   TemperaturFurther, the solution was warmed to room temperature
5. 5
   workup.STIRRINGstirred for 3 hours
6. 6
   workup.STIRRINGAfter stirring
7. 7
   Extraktionextracted with toluene (50 ml×3)
8. 8
   WaschenThe organic layer was washed with water
9. 9
   Trocknendried over anhydrous magnesium sulfate
10. 10
    Einengenconcentrated under reduced pressure

Vorschrift

In a flask equipped with a stirrer, a thermometer and a dropping funnel, 3.36 g of sodium hydride was dissolved in 50 ml of THF under nitrogen atmosphere and the solution was cooled down to −5° C. with stirring. 30 ml of a THF solution of ethyl diethylphosphinoacetate (18.8 g) was added dropwise thereto, and the solution was further stirred for 2 hours. After observing hydrogen gas generation, 50 ml of a THF solution of trans-4-(trans-4-propylcyclohexyl)-cyclohexanecarbaldehyde (16.5 g) was added dropwise. Further, the solution was warmed to room temperature and stirred for 3 hours. After stirring, water was added to the reaction mixture and extracted with toluene (50 ml×3). The organic layer was washed with water, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure to obtain 10.0 g of ethyl 3-(trans-4-(trans-4-propylcyclohexyl)cyclohexyl)propenoate.

Quelle