tert-Butyl hydroperoxide → Acetic acid 1-(4-bromo-3-methoxy-5,5-dimethyl-8-oxo-5,6,7,8-tetrahydro-naphthalen-2-yl)-ethyl ester

HRID 2180595ノート

反応式

HRID 2180595 の反応式
[C:1]([O:5]O)([CH3:4])([CH3:3])C.[Br:7][C:8]1[C:17]2[C:16]([CH3:19])([CH3:18])[CH2:15]CCC=2[CH:11]=[C:10]([CH:20]([O:22][C:23](=[O:25])[CH3:24])[CH3:21])[C:9]=1[O:26][CH3:27]>ClCCl.[O-2].[Cr+6].[O-2].[O-2]>[Br:7][C:8]1[C:17]2[C:16]([CH3:18])([CH3:19])[CH2:15][CH2:4][C:1](=[O:5])[C:3]=2[CH:11]=[C:10]([CH:20]([O:22][C:23](=[O:25])[CH3:24])[CH3:21])[C:9]=1[O:26][CH3:27]

参加物

5

反応物 2

HCID 6410tert-Butyl hydroperoxideHCID 69731470Acetic acid 1-(4-bromo-3-methoxy-5,5-dimethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-ethyl ester

生成物 1

HCID 69730619Acetic acid 1-(4-bromo-3-methoxy-5,5-dimethyl-8-oxo-5,6,7,8-tetrahydro-naphthalen-2-yl)-ethyl ester

試薬・触媒・溶媒 2

HCID 10219390chromium (VI) trioxide触媒HCID 6344Dichloromethane溶媒2 回

実験手順

To a suspension of chromium (VI) oxide (160 mg, 1.6 mmol) in dichloromethane (40 mL) at 0° C. was added tert-butyl hydroperoxide (13 mL, 96 mmol). After stirring at room temperature for 5 min, a solution of acetic acid 1-(4-bromo-3-methoxy-5,5-dimethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-ethyl ester (Compound A-97, 11.4 g, 32 mmol) in dichloromethane (10 mL) was added. The mixture was stirred at room temperature for 6 days and then quenched with 10% sodium bisulfite.). Organic phase was washed with 10% sodium bisulfite and brine, dried (Na2SO4), filtered and concentrated in vacuo. Recrystallization from ethyl acetate and flash column chromatography of the mother liquid (silica gel, 10% ethyl acetate in hexane) afforded the title compound as a yellow solid.

後処理

  1. stirringThe mixture was stirred at room temperature for 6 days
  2. customquenched with 10% sodium bisulfite
  3. washOrganic phase was washed with 10% sodium bisulfite and brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customRecrystallization from ethyl acetate and flash column chromatography of the mother liquid (silica gel, 10% ethyl acetate in hexane)

出典と根拠

ORDレコード
ord-d932314b7ca44f6d9f946f8bac0e72b3
出典データセット
uspto-grants-2005_05
特許番号
US06887896B1

反応ノート

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