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1-Bromo-3-(trimethylsiloxy)benzene → 4-(3-hydroxyphenyl)-4-hydroxy-7-methoxymethyloxy-3-[4-(methoxymethyloxy)phenyl]-2,3-dihydro-4H-benzopyran

HRID 1859327
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인쇄 미리보기

반응식

HRID 1859327 반응식
C[Si]([O:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8](Br)[CH:7]=1)(C)C.[Mg].[CH3:14][O:15][CH2:16][O:17][C:18]1[CH:38]=[CH:37][C:21]2[C:22](=[O:36])[CH:23]([C:26]3[CH:31]=[CH:30][C:29]([O:32][CH2:33][O:34][CH3:35])=[CH:28][CH:27]=3)[CH2:24][O:25][C:20]=2[CH:19]=1>O1CCCC1>[OH:5][C:6]1[CH:7]=[C:8]([C:22]2([OH:36])[C:21]3[CH:37]=[CH:38][C:18]([O:17][CH2:16][O:15][CH3:14])=[CH:19][C:20]=3[O:25][CH2:24][CH:23]2[C:26]2[CH:31]=[CH:30][C:29]([O:32][CH2:33][O:34][CH3:35])=[CH:28][CH:27]=2)[CH:9]=[CH:10][CH:11]=1
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 6158011-Bromo-3-(trimethylsiloxy)benzeneHCID 5462224MagnesiumHCID 221236097-Methoxymethoxy-3-(4-methoxymethoxyphenyl)chroman-4-one

생성물 1

HCID 221235924-(3-hydroxyphenyl)-4-hydroxy-7-methoxymethyloxy-3-[4-(methoxymethyloxy)phenyl]-2,3-dihydro-4H-benzopyran수율 92.2%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran
용매
2회

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온도
-78 °C

실험 절차

Under nitrogen atmosphere 3-bromomagnesium phenyl trimethylsilyl ether was prepared from 3-bromophenyl trimethylsilyl ether (629 mg, 2.1 mmol) and magnesium turning (52 mg, 2.1 mmol) in dry tetrahydrofuran (1.5 ml) and then cooled to -78° C. 7-Methoxymethyloxy-3-[4-(methoxymethyloxy)phenyl]-2,3-dihydro-benzopyran-4-one (250 mg, 0.7 mmol) dissolved in dry tetrahydrofuran (2 ml) was slowly added dropwise thereto and then stirred for one hour. The reaction solution was quenched with saturated aqueous ammonium chloride solution and extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure to remove the organic solvent. The concentrate was separated by column chromatography (n-hexane:ethyl acetate=4:1) to obtain 283 mg (yield: 92%) of the title compound as a foam.

후처리

  1. additionwas slowly added dropwise
  2. customThe reaction solution was quenched with saturated aqueous ammonium chloride solution
  3. extractionextracted with ethyl acetate
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customto remove the organic solvent
  7. customThe concentrate was separated by column chromatography (n-hexane:ethyl acetate=4:1)

출처 및 근거

ORD 기록
ord-da01f61b237d493697a7d0acca2906b1
출처 데이터셋
uspto-grants-2000_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06153768

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