Reaktion #489162

Reaktionsgleichung

1-bromo-4-cyclohexyloxy-benzene

cyclohexylmethylketone

(R)-(+)-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl

potassium t-butoxide

→

1-cyclohexyl-2-(4-cyclohexyloxy-phenyl)-ethanone

Ausbeute 29.7%

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe reaction was cooled
2. 2
   Sonstigepartitioned in water (50 mL)
3. 3
   FiltrationThe mixture was filtered
4. 4
   Filtrationthrough fluted filter paper
5. 5
   Sonstigethe layers were separated
6. 6
   WaschenThe aqueous layer was washed with diethyl ether (3×20 mL)
7. 7
   WaschenThe combined organic layers were washed with brine (10 mL)
8. 8
   Trocknendried (Na2SO4)
9. 9
   Filtrationfiltered
10. 10
    Einengenconcentrated under reduced pressure
11. 11
    SonstigeThe crude product was purified on a 24 g SiO2 cartridge

Vorschrift

A stirred suspension of 1-bromo-4-cyclohexyloxy-benzene (3.92 mmol, 1.0 g), cyclohexylmethylketone (5.92 mmol, 0.83 mL), (R)-(+)-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (1.88 mmol, 1.17 g), tris(dibenzylideneacetone)dipalladium(0) (0.78 mmol, 0.72 g), and potassium t-butoxide (7.84 mmol, 0.88 g) were heated to 90° C. for 12 h in a sealed vial. The reaction was cooled and partitioned in water (50 mL) and diethyl ether (50 mL). The mixture was filtered through fluted filter paper and the layers were separated. The aqueous layer was washed with diethyl ether (3×20 mL). The combined organic layers were washed with brine (10 mL), dried (Na2SO4), filtered, and concentrated under reduced pressure. The crude product was purified on a 24 g SiO2 cartridge using an ethyl acetate/hexanes gradient to give 1-cyclohexyl-2-(4-cyclohexyloxy-phenyl)-ethanone (0.35 g).

Quelle