Reaktion #1544577

Reaktionsgleichung

NaH

toluene

cyclohexanol

1-bromonaphthalene

toluene

→

1-naphthyl cyclohexyl ether

Ausbeute 60.0%

Lösungsmittel

diethyl ether

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeAn oven dried Schlenk tube
2. 2
   Sonstigeequipped with a teflon coated stir bar
3. 3
   workup.ADDITIONwere added
4. 4
   SonstigeThe aqueous layer was separated
5. 5
   Extraktionextracted with diethyl ether (60 mL)
6. 6
   Waschenwashed with brine (60 mL)
7. 7
   Trocknendried over anhydrous MgSO4
8. 8
   SonstigeThe drying agent was removed by filtration
9. 9
   Einengenthe mother liquor concentrated in vacuo
10. 10
    SonstigeThe crude product was purified by flash chromatography on silica gel (50:1 hexanes:ethyl acetate)

Vorschrift

An oven dried Schlenk tube equipped with a teflon coated stir bar was charged with NaH (40 mg, 1.50 mmol), toluene (2 mL) and cyclohexanol (94 μL, 0.90 mmol). The mixture was heated to 70° C. for 10 min under an atmosphere of argon. To this was added 1-bromonaphthalene (104 μL, 0.75 mmol), Pd2 (dba)3 (10.3 mg, 0.0113 mmol), (R)-(+)-2,2'-bis(di-p-tolylphosphino)-1,1'-binaphthyl (Tol-BINAP) (18.3 mg, 0.027 mmol), and 2 mL of toluene. The mixture was heated to 70° C. for 20 h at which time water (60 mL) and diethyl ether (60 mL) were added. The aqueous layer was separated and extracted with diethyl ether (60 mL). The organics were combined, washed with brine (60 mL) and dried over anhydrous MgSO4. The drying agent was removed by filtration and the mother liquor concentrated in vacuo. The crude product was purified by flash chromatography on silica gel (50:1 hexanes:ethyl acetate) to afford 1-naphthyl cyclohexyl ether (101 mg, 60% yield) as a colorless oil.

Quelle