반응 #438514

반응 방정식

ammonium chloride

4-bromoiodobenzene

isopropyl magnesium chloride

8-dimethylamino-1,4-dioxaspiro[4.5]decane-8-carbonitrile

→

4-(4-bromophenyl)-4-dimethylamino-1-phenethylcyclohexanol

용매

diethylether

diethylether

반응 조건

후처리

1. 1
   workup.ADDITIONwere added dropwise
2. 2
   workup.ADDITIONwere added
3. 3
   추출extracted three times with 100 ml diethylether in each case
4. 4
   건조the combined organic phases were dried over sodium sulfate
5. 5
   여과filtered
6. 6
   농축concentrated
7. 7
   기타The crude product (21.8 g) obtained
8. 8
   기타was chromatographed with diethylether over silica gel

실험 절차

26.6 g 4-bromoiodobenzene were placed in 150 ml diethylether and 47 ml 2.0 molar isopropyl magnesium chloride solution were added dropwise at ambient temperature. After one further hour, 18 g 8-dimethylamino-1,4-dioxaspiro[4.5]decane-8-carbonitrile, dissolved in 250 ml diethylether, were added dropwise and stirred overnight. To work up the mixture with ice cooling, 20 ml ammonium chloride solution (20% by weight) were added, extracted three times with 100 ml diethylether in each case, the combined organic phases were dried over sodium sulfate, filtered, concentrated and substantially freed of solvent residues under vacuum. The crude product (21.8 g) obtained was chromatographed with diethylether over silica gel. 7.49 g 4-(4-bromophenyl)-4-dimethylamino-1-phenethylcyclohexanol were obtained as a colorless liquid.

출처