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 2180595노트

반응식

HRID 2180595 반응식
[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]

참가 물질

5

반응물 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

생성물 1

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

시약·촉매·용매 2

HCID 10219390chromium (VI) trioxide촉매HCID 6344Dichloromethane용매2회

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-d932314b7ca44f6d9f946f8bac0e72b3
출처 데이터셋
uspto-grants-2005_05
특허 번호
US06887896B1

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