반응 #77444

반응 방정식

KOH

H2O

HCF2Cl

11-Benzyl-11-aza-tricyclo[7.3.1.02,7]trideca-2(7),3,5-trien-5-ol

→

11-BENZYL-5-DIFLUOROMETHOXY-11-AZA-TRICYCLO[7.3.1.02,7]TRIDECA-2(7),3,5-TRIENE

용매

dioxane

반응 조건

후처리

1. 1
   온도to maintain a pH˜12
2. 2
   기타The consumption of starting material
3. 3
   기타was monitored by TLC for over 2 hours
4. 4
   온도The reaction was cooled
5. 5
   workup.ADDITIONdiluted with H2O (40 mL)
6. 6
   추출extracted with EtOAc
7. 7
   세척The organic layer was washed with a sat. aq. Na2CO3 soln
8. 8
   건조(25 mL) and brine (25 mL), dried (MgSO2)
9. 9
   여과filtered
10. 10
    농축concentrated to an oil (620 mg, 92%)

실험 절차

11-Benzyl-11-aza-tricyclo[7.3.1.02,7]trideca-2(7),3,5-trien-5-ol (572 mg, 2.05 mmol) was stirred in dioxane (5 mL) and H2O (1 mL) at reflux under a balloon of freon (HCF2Cl). To this was added 3N KOH dropwise so as to maintain a pH˜12. The consumption of starting material was monitored by TLC for over 2 hours. The reaction was cooled, diluted with H2O (40 mL) and extracted with EtOAc. The organic layer was washed with a sat. aq. Na2CO3 soln. (25 mL) and brine (25 mL), dried (MgSO2), filtered and concentrated to an oil (620 mg, 92%). GCMS m/e 329 (M+).

출처