반응 #7937

반응 방정식

EtSH

AlCl3

HCl

NaHCO3

9a-butyl-7-methoxy-4-{4-[2-(1-piperidinyl)-ethoxy]phenyl}-1,2,9,9a-tetrahydro-3H-fluoren-3-one

→

9a-butyl-7-hydroxy-4-{4-[2-(1-piperidinyl)ethoxy]phenyl}-1,2,9,9a-tetrahydro-3H-fluoren-3-one

용매

EtOAc

water

tetrahydrofuran

CH2Cl2

반응 조건

후처리

1. 1
   기타contained in an ice-cold flask
2. 2
   workup.WAITat room temperature for 35 minutes
3. 3
   온도The mixture was cooled in an ice bath
4. 4
   workup.STIRRINGstirred at 0° C. for 10 minutes
5. 5
   workup.STIRRINGstirred
6. 6
   기타The layers were separated
7. 7
   추출the aqueous portion extracted with EtOAc
8. 8
   세척The combined organics were washed with brine
9. 9
   건조dried over MgSO4
10. 10
    여과filtered
11. 11
    기타evaporated under vacuum

실험 절차

An ice-cold solution of 9a-butyl-7-methoxy-4-{4-[2-(1-piperidinyl)-ethoxy]phenyl}-1,2,9,9a-tetrahydro-3H-fluoren-3-one (85 mg, 96% weight pure, 0.172 mmol) in anhydrous CH2Cl2 (1.2 mL) was placed under a nitrogen atmosphere and treated with EtSH (0.055 mL, 0.743 mmol). The resulting solution was added by syringe to AlCl3 (115.2 mg, 0.864 mmol) contained in an ice-cold flask and kept under nitrogen. The resulting solution was stirred at 0° C. for 3 minutes, then at room temperature for 35 minutes. The mixture was cooled in an ice bath, treated with 0.5N HCl (1.6 mL) and tetrahydrofuran (1.0 mL), and stirred at 0° C. for 10 minutes. The resulting mixture was diluted with EtOAc (20 mL) and water (15 mL) and stirred while basifying with solid NaHCO3. The layers were separated and the aqueous portion extracted with EtOAc. The combined organics were washed with brine, dried over MgSO4, filtered, and evaporated under vacuum to afford 9a-butyl-7-hydroxy-4-{4-[2-(1-piperidinyl)ethoxy]phenyl}-1,2,9,9a-tetrahydro-3H-fluoren-3-one as a yellow semi-solid.

출처