Réaction #2028911

Équation de réaction

Toluene

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

diisobutylaluminum hydride toluene

→

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

Rendement 99.6%

Solvants

formic acid

Conditions de réaction

Traitement

1. 1
   Autreprepared in the first step
2. 2
   Autreto give two layers
3. 3
   ExtractionThe water layer was extracted with toluene (10 ml) twice
4. 4
   Lavagethe combined organic layer was washed with water
5. 5
   Séchagedried over anhydrous magnesium sulfate
6. 6
   workup.DISTILLATIONThe solvent was distilled off under reduced pressure

Mode opératoire

Toluene (10 ml) was added to 6-propyl-3-(2,2′,3,3′-tetrafluoro-4′-(6-pentyltetrahydro-2H-pyran-3-yl)biphenyl-4-yl)tetrahydro-2H-pyran-2-one (20) (1.2 g) prepared in the first step. A diisobutylaluminum hydride-toluene solution (0.99 M; 3.49 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 (15 ml) to give two layers. The water layer was extracted with toluene (10 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 6-propyl-3-(2,2′,3,3′-tetrafluoro-4′-(6-pentyltetrahydro-2H-pyran-3-yl)biphenyl-4-yl)tetrahydro-2H-pyran-2-ol (21) (1.2 g) in 98% yield.

Source