Reacción #2028907

Ecuación de reacción

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

Rendimiento 99.0%

Disolventes

formic acid

Condiciones de reacción

Tratamiento posterior

1. 1
   Otroprepared in the ninth step
2. 2
   Otroto give two layers
3. 3
   ExtracciónThe water layer was extracted with toluene (20 ml) twice
4. 4
   Lavadothe combined organic layer was washed with water
5. 5
   Secadodried over anhydrous magnesium sulfate
6. 6
   workup.DISTILLATIONThe solvent was distilled off under reduced pressure

Procedimiento

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.

Fuente