반응 #2028908

반응 방정식

Dichloromethane

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

Triethylsilane

→

5-(4′-ethoxy-2,2′,3,3′-tetrafluorobiphenyl-4-yl)-2-(4-propylcyclohexyl)tetrahydropyran

수율 36.1%

용매

water

반응 조건

후처리

1. 1
   기타prepared in the tenth step
2. 2
   기타to give two layers
3. 3
   세척The organic layer was washed with water
4. 4
   건조dried over anhydrous magnesium sulfate
5. 5
   workup.DISTILLATIONThe solvent was distilled off under reduced pressure
6. 6
   기타The residue was purified by silica gel chromatography (silica gel: 200 g, eluent: heptane/ethyl acetate=80/20 by volume)
7. 7
   기타by recrystallization (heptane/ethyl acetate=90/10 by volume)

실험 절차

Dichloromethane (30 ml) was added to 3-(4′-ethoxy-2,2′,3,3′-tetrafluorobiphenyl-4-yl)-6-(4-propylcyclohexyl)tetrahydropyran-2-ol (12) (2.29 g) prepared in the tenth step. Triethylsilane (1.93 g) and a boron trifluoride-diethyl ether complex (2.37 g) were added dropwise to the solution at −30° C. After 3 hours of stirring, water (30 ml) was added to give two layers. The organic layer was washed with water, dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure. The residue was purified by silica gel chromatography (silica gel: 200 g, eluent: heptane/ethyl acetate=80/20 by volume) and then by recrystallization (heptane/ethyl acetate=90/10 by volume) to give 5-(4′-ethoxy-2,2′,3,3′-tetrafluorobiphenyl-4-yl)-2-(4-propylcyclohexyl)tetrahydropyran (13) (0.8 g) in 36% yield.

출처