반응 #7938

반응 방정식

2-propanethiol

9a-butyl-4-(4-hydroxy-phenyl)-7-methoxy-1,2,9,9a-tetrahydro-3H-fluoren-3-one

AlCl3

HCl

→

9a-BUTYL-7-HYDROXY-4-(4-HYDROXYPHENYL)-1,2,9,9a-TETRAHYDRO-3H-FLUOREN-3-ONE

용매

CH2Cl2

EtOAc

반응 조건

후처리

1. 1
   기타contained in an ice cooled flask
2. 2
   workup.STIRRINGThe resulting mixture was stirred at 0° C. for 5 minutes and at room temperature for 3.25 hours
3. 3
   workup.STIRRINGstirred for 15 minutes at room temperature
4. 4
   기타The EtOAc layer was separated
5. 5
   세척washed with 1N HCl and brine
6. 6
   건조dried over MgSO4
7. 7
   여과filtered
8. 8
   기타evaporated under vacuum
9. 9
   기타to give a yellow gum
10. 10
    기타This material was triturated with benzene
11. 11
    기타to give
12. 12
    여과after filtration
13. 13
    건조drying under vacuum, 9a-butyl-7-hydroxy-4-(4-hydroxyphenyl)-1,2,9,9a-tetrahydro-3H-fluoren-3-one as an off-white solid

실험 절차

An ice-cold solution of 9a-butyl-4-(4-hydroxy-phenyl)-7-methoxy-1,2,9,9a-tetrahydro-3H-fluoren-3-one (29 mg, 0.08 mmol) in anhydrous CH2Cl2 (1 mL) was added to AlCl3 (96 mg, 0.72 mmol) contained in an ice cooled flask. The mixture was stirred at 0° C. under a nitrogen atmosphere and treated with 2-propanethiol (0.056 mL, 0.6 mmol). The resulting mixture was stirred at 0° C. for 5 minutes and at room temperature for 3.25 hours, then treated with ice (approx. 2 mL), 2N HCl (2 mL) and EtOAc (4 mL) and stirred for 15 minutes at room temperature. The EtOAc layer was separated, washed with 1N HCl and brine, dried over MgSO4, filtered, and evaporated under vacuum to give a yellow gum. This material was triturated with benzene to give, after filtration and drying under vacuum, 9a-butyl-7-hydroxy-4-(4-hydroxyphenyl)-1,2,9,9a-tetrahydro-3H-fluoren-3-one as an off-white solid.

출처