Reaktion #49660

Reaktionsgleichung

ammonium chloride

8-benzylidene-9-azatricyclo[4.3.1.04,9 ]decan-7-one

phenyl magnesium bromide

→

white solid

Ausbeute 53.0%

8-(Diphenylmethyl)-9-azatricyclo[4.3.1.04,9 ]decan-7-one

Ausbeute 53.0%

Lösungsmittel

toluene

ether

toluene

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeTo a 100 ml three-necked round-bottomed flask equipped with a rubber septum and nitrogen inlet
2. 2
   ExtraktionThe mixture was extracted into ethyl acetate
3. 3
   Waschenthe organic layer washed with saturated aqueous ammonium chloride and brine
4. 4
   Trocknendried over sodium sulfate
5. 5
   Sonstigeevaporated
6. 6
   SonstigeThe residue was chromatographed on silica gel

Vorschrift

To a 100 ml three-necked round-bottomed flask equipped with a rubber septum and nitrogen inlet were added 5 ml dry toluene and 4.43 ml (13.3 mmol) of a 3.0M solution of phenyl magnesium bromide in ether. The solution was cooled to 0° C., and a solution of 2.07 g (8.87 mmol) 8-benzylidene-9-azatricyclo[4.3.1.04,9 ]decan-7-one in 20 ml toluene was added over 5 min. The reaction was allowed to stir at 0° C. for 1 hour and then poured into saturated aqueous ammonium chloride. The mixture was extracted into ethyl acetate, and the organic layer washed with saturated aqueous ammonium chloride and brine, dried over sodium sulfate, and evaporated. The residue was chromatographed on silica gel using hexane/ethyl acetate as eluent and the product fractions combined to afford 1.47 g (53%) of a white solid, mp 137°-138° C.

Quelle