反応 #7938

反応方程式

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

溶媒

CH2Cl2

EtOAc

反応条件

後処理

1. 1
   その他contained 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
   その他The EtOAc layer was separated
5. 5
   洗浄washed with 1N HCl and brine
6. 6
   乾燥dried over MgSO4
7. 7
   ろ過filtered
8. 8
   その他evaporated under vacuum
9. 9
   その他to give a yellow gum
10. 10
    その他This material was triturated with benzene
11. 11
    その他to give
12. 12
    ろ過after filtration
13. 13
    乾燥drying under vacuum, 9a-butyl-7-hydroxy-4-(4-hydroxyphenyl)-1,2,9,9a-tetrahydro-3H-fluoren-3-one as an off-white solid

実験手順

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.

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