Reacción #77444

Ecuación de reacción

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

Disolventes

dioxane

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturato maintain a pH˜12
2. 2
   OtroThe consumption of starting material
3. 3
   Otrowas monitored by TLC for over 2 hours
4. 4
   TemperaturaThe reaction was cooled
5. 5
   workup.ADDITIONdiluted with H2O (40 mL)
6. 6
   Extracciónextracted with EtOAc
7. 7
   LavadoThe organic layer was washed with a sat. aq. Na2CO3 soln
8. 8
   Secado(25 mL) and brine (25 mL), dried (MgSO2)
9. 9
   Filtraciónfiltered
10. 10
    Concentraciónconcentrated to an oil (620 mg, 92%)

Procedimiento

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+).

Fuente