Réaction #2028913

Équation de réaction

magnesium

THF

iodine

4-(2-Bromoethyl)-4′-ethoxy-2,2′,3,3′-tetrafluorobiphenyl

THF

5-(4-propylcyclohexyl)tetrahydro-2H-pyran-2-one

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

THF

→

2-(2-(4′-ethoxy-2,2′,3,3′-tetrafluorobiphenyl-4-yl)ethyl)-5-(4-propylcyclohexyl)tetrahydro-2H-pyran-2-ol

Rendement 47.1%

Conditions de réaction

Traitement

1. 1
   workup.ADDITIONAfter the addition
2. 2
   Autreit was quenched with a saturated aqueous solution of ammonium chloride, and water (20 ml)
3. 3
   workup.ADDITIONwas added
4. 4
   Autreto give two layers
5. 5
   ExtractionThe water layer was extracted with toluene (10 ml) twice
6. 6
   Lavagethe combined organic layer was washed with water
7. 7
   Séchagedried over anhydrous magnesium sulfate
8. 8
   workup.DISTILLATIONThe solvent was distilled off under reduced pressure
9. 9
   AutreThe residue was purified by silica gel chromatography (silica gel: 20 g, eluent: toluene/ethyl acetate=70/30 by volume)

Mode opératoire

THF (5 ml) was added to magnesium turnings (0.30 g) in a reaction vessel under an atmosphere of nitrogen, and a minute amount of iodine was added. 4-(2-Bromoethyl)-4′-ethoxy-2,2′,3,3′-tetrafluorobiphenyl (29) (4.60 g) in a THF (5 ml) solution was slowly added dropwise at a temperature 50° C. or lower. After the addition had been completed, the stirring was continued at room temperature for 30 minutes. The reaction mixture was then cooled to −30° C. or lower, and 5-(4-propylcyclohexyl)tetrahydro-2H-pyran-2-one (20) (2.46 g) in a THF (5 ml) solution was added dropwise. After the reaction mixture had been stirred at room temperature for 5 hours, it was quenched with a saturated aqueous solution of ammonium chloride, and water (20 ml) was added 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. The residue was purified by silica gel chromatography (silica gel: 20 g, eluent: toluene/ethyl acetate=70/30 by volume) to give 2-(2-(4′-ethoxy-2,2′,3,3′-tetrafluorobiphenyl-4-yl)ethyl)-5-(4-propylcyclohexyl)tetrahydro-2H-pyran-2-ol (30) (2.7 g) in 47.1% yield.

Source