반응 #49660

반응 방정식

ammonium chloride

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

phenyl magnesium bromide

→

white solid

수율 53.0%

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

수율 53.0%

용매

toluene

ether

toluene

반응 조건

후처리

1. 1
   기타To a 100 ml three-necked round-bottomed flask equipped with a rubber septum and nitrogen inlet
2. 2
   추출The mixture was extracted into ethyl acetate
3. 3
   세척the organic layer washed with saturated aqueous ammonium chloride and brine
4. 4
   건조dried over sodium sulfate
5. 5
   기타evaporated
6. 6
   기타The residue was chromatographed on silica gel

실험 절차

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.

출처