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

HRID 7842

反応式

HRID 7842 の反応式
[CH2:1]([C:5]12[CH2:17][CH2:16][C:15](=[O:18])[C:14]([C:19]3[CH:24]=[CH:23][C:22]([OH:25])=[CH:21][CH:20]=3)=[C:13]1[C:12]1[C:7](=[CH:8][C:9]([O:26]C)=[CH:10][CH:11]=1)[CH2:6]2)[CH2:2][CH2:3][CH3:4].[Al+3].[Cl-].[Cl-].[Cl-].CC(S)C.Cl>C(Cl)Cl.CCOC(C)=O>[CH2:1]([C:5]12[CH2:17][CH2:16][C:15](=[O:18])[C:14]([C:19]3[CH:20]=[CH:21][C:22]([OH:25])=[CH:23][CH:24]=3)=[C:13]1[C:12]1[C:7](=[CH:8][C:9]([OH:26])=[CH:10][CH:11]=1)[CH2:6]2)[CH2:2][CH2:3][CH3:4]

参加物

7

反応物 4

HCID 313Hydrochloric AcidHCID 63642-PropanethiolHCID 6451240Aluminum(III) ChlorideHCID 219909159a-butyl-4-(4-hydroxyphenyl)-7-methoxy-1,2,9,9a-tetrahydro-3H-fluoren-3-one

生成物 1

HCID 101547809a-BUTYL-7-HYDROXY-4-(4-HYDROXYPHENYL)-1,2,9,9a-TETRAHYDRO-3H-FLUOREN-3-ONE

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
0 °C

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.

後処理

  1. customcontained in an ice cooled flask
  2. stirringThe resulting mixture was stirred at 0° C. for 5 minutes and at room temperature for 3.25 hours
  3. stirringstirred for 15 minutes at room temperature
  4. customThe EtOAc layer was separated
  5. washwashed with 1N HCl and brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. customevaporated under vacuum
  9. customto give a yellow gum
  10. customThis material was triturated with benzene
  11. customto give
  12. filtrationafter filtration
  13. dry with materialdrying under vacuum, 9a-butyl-7-hydroxy-4-(4-hydroxyphenyl)-1,2,9,9a-tetrahydro-3H-fluoren-3-one as an off-white solid

出典と根拠

ORDレコード
ord-97264f6f2909414bad48b9659123da7c
出典データセット
uspto-grants-2006_08
特許番号
US07087599B2

関連ノート

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