Reaktion #2028907

Reaktionsgleichung

Toluene

3-(4′-ethoxy-2,2′,3,3′-tetrafluorobiphenyl-4-yl)-6-(4-propylcyclohexyl)tetrahydropyran-2-one

toluene

diisobutylaluminum hydride

→

3-(4′-ethoxy-2,2′,3,3′-tetrafluorobiphenyl-4-yl)-6-(4-propylcyclohexyl)tetrahydropyran-2-ol

Ausbeute 99.0%

Lösungsmittel

formic acid

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigeprepared in the ninth 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
   Trocknendried over anhydrous magnesium sulfate
6. 6
   workup.DISTILLATIONThe solvent was distilled off under reduced pressure

Vorschrift

Toluene (20 ml) was added to 3-(4′-ethoxy-2,2′,3,3′-tetrafluorobiphenyl-4-yl)-6-(4-propylcyclohexyl)tetrahydropyran-2-one (11) (2.35 g) prepared in the ninth step. A toluene solution of diisobutylaluminum hydride (0.99 M; 9.6 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, and then dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure to leave 3-(4′-ethoxy-2,2′,3,3′-tetrafluorobiphenyl-4-yl)-6-(4-propylcyclohexyl)tetrahydropyran-2-ol (12) (2.29 g) in 99% yield.

Quelle