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

HRID 1859318
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인쇄 미리보기

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HRID 1859318 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:39]=[CH:38][C:21]2[C:22](=[O:37])[C:23]([C:27]3[CH:32]=[CH:31][C:30]([O:33][CH2:34][O:35][CH3:36])=[CH:29][CH:28]=3)([CH3:26])[CH2:24][O:25][C:20]=2[CH:19]=1>O1CCCC1>[OH:37][C:22]1([C:8]2[CH:9]=[CH:10][CH:11]=[C:6]([OH:5])[CH:7]=2)[C:21]2[CH:38]=[CH:39][C:18]([O:17][CH2:16][O:15][CH3:14])=[CH:19][C:20]=2[O:25][CH2:24][C:23]1([C:27]1[CH:32]=[CH:31][C:30]([O:33][CH2:34][O:35][CH3:36])=[CH:29][CH:28]=1)[CH3:26]
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참가 물질

5

반응물 3

HCID 6158011-Bromo-3-(trimethylsiloxy)benzeneHCID 5462224MagnesiumHCID 154817637-Methoxymethoxy-3-(4-methoxymethoxyphenyl)-3-methylchroman-4-one

생성물 1

HCID 22123575(3RS,4RS)-4-hydroxy-4-(3-hydroxyphenyl)-7-methoxymethyloxy-3-[4-(methoxymethyloxy)phenyl]-3-methyl-2,3-dihydro-4H-benzopyran수율 67%

시약·촉매·용매 1

HCID 8028
Tetrahydrofuran
용매
2회

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온도
0 °C

실험 절차

Under argon atmosphere 3-bromomagnesium phenyl trimethylsilyl ether was prepared from 3-bromophenyl trimethylsilyl ether (3 g, 12.24 mmol) and magnesium turning (300 mg, 12.34 mmol) in dry tetrahydrofuran (10 ml) and cooled to 0° C. 7-Methoxymethyloxy-3-[4-(methoxymethyloxy)phenyl]-3-methyl-2,3-dihydro-4H-benzopyran-4-one (900 mg, 2.51 mmol) dissolved in dry tetrahydrofuran (5 ml) was slowly added dropwise thereto and then refluxed for 12 hours. The reaction mixture was cooled to room temperature, quenched with water and then 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=2:1) to obtain 760 mg (yield: 67%) of the title compound as a foam.

후처리

  1. additionwas slowly added dropwise
  2. temperaturerefluxed for 12 hours
  3. temperatureThe reaction mixture was cooled to room temperature
  4. customquenched with water
  5. extractionextracted with ethyl acetate
  6. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customto remove the organic solvent
  9. customThe concentrate was separated by column chromatography (n-hexane:ethyl acetate=2:1)

출처 및 근거

ORD 기록
ord-78a900149b83476bb73ac7e85683b9aa
출처 데이터셋
uspto-grants-2000_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06153768

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