Reaktion #2028909

Reaktionsgleichung

Toluene

6-propyl-3-(2,2′,3,3′-tetrafluoro-4′-(4-propylcyclohexyl)biphenyl-4-yl)tetrahydro-2H-pyran-2-one

diisobutylaluminum hydride toluene

→

6-propyl-3-(2,2′,3,3′-tetrafluoro-4′-(4-propylcyclohexyl)biphenyl-4-yl)tetrahydro-2H-pyran-2-ol

Ausbeute 100.1%

Lösungsmittel

formic acid

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigeprepared in the first step
2. 2
   Sonstigeto give two layers
3. 3
   ExtraktionThe water layer was extracted with toluene (20 ml) twice
4. 4
   Waschenthe combined organic layer was washed with water
5. 5
   TrocknenThe solution was dried over anhydrous magnesium sulfate
6. 6
   workup.DISTILLATIONThe solvent was distilled off under reduced pressure

Vorschrift

Toluene (50 ml) was added to 6-propyl-3-(2,2′,3,3′-tetrafluoro-4′-(4-propylcyclohexyl)biphenyl-4-yl)tetrahydro-2H-pyran-2-one (16) (4.18 g) prepared in the first step. A diisobutylaluminum hydride-toluene solution (0.99 M; 12.5 ml) was added dropwise at −50° C. or lower, and the stirring was continued for 3 hours. The reaction mixture was poured into a 10% aqueous solution of formic acid (50 ml) to give two layers. The water layer was extracted with toluene (20 ml) twice and the combined organic layer was washed with water. The solution was dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure to leave 6-propyl-3-(2,2′,3,3′-tetrafluoro-4′-(4-propylcyclohexyl)biphenyl-4-yl)tetrahydro-2H-pyran-2-ol (17) (4.2 g) in 99% yield.

Quelle