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2-Methoxyethanol → 2-Phenoxy-3-[3-(3-methoxyethoxypyridin-4-yl)propoxy]pyridine

HRID 1841564
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HRID 1841564 반응식
[CH3:1][O:2][CH2:3][CH2:4]O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O.[O:39]([C:46]1[C:51]([O:52][CH2:53][CH2:54][CH2:55][C:56]2[CH:61]=[CH:60][N:59]=[CH:58][C:57]=2[OH:62])=[CH:50][CH:49]=[CH:48][N:47]=1)[C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1>C1COCC1>[O:39]([C:46]1[C:51]([O:52][CH2:53][CH2:54][CH2:55][C:56]2[CH:61]=[CH:60][N:59]=[CH:58][C:57]=2[O:62][CH2:4][CH2:3][O:2][CH3:1])=[CH:50][CH:49]=[CH:48][N:47]=1)[C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1
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참가 물질

6

반응물 4

HCID 80192-MethoxyethanolHCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 98836252-Phenoxy-3-[3-(3-hydroxypyridin-4-yl)propoxy]pyridine

생성물 1

HCID 178146312-Phenoxy-3-[3-(3-methoxyethoxypyridin-4-yl)propoxy]pyridine

시약·촉매·용매 1

HCID 8028
Tetrahydrofuran
용매

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온도
60 °C

실험 절차

2-Methoxyethanol (0.08 g, 0.93 mmol) and triphenylphosphine (0.32 g, 1.2 mmol) are dissolved in THF (20 ml), and thereto are successively added with stirring diisopropyl azodicarboxylate (0.17 g, 0.93 mmol) and 2-phenoxy-3-[3-(3-hydroxypyridin-4-yl)propoxy]pyridine (0.20 g, 0.62 mmol) obtained in Example 30 under ice-cooling. The mixture is further stirred at 60° C. for one hour, and the reaction solution is concentrated under reduced pressure. To the residue is added ethyl acetate (50 ml), and the mixture is extracted with a 10% aqueous hydrochloric acid solution (50 ml×2). The pH value of the aqueous layer is adjusted to pH 12 with potassium carbonate, and the mixture is extracted with ethyl acetate (50 ml×2). The organic layer is washed with a saturated brine (50 ml×2), dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue is purified by silica gel column chromatography (eluent: ethyl acetate/methanol) to give 2-phenoxy-3-[3-(3-methoxyethoxypyridin-4-yl)propoxy]pyridine, which is further treated with fumaric acid to give the title compound (0.12 g), m.p. 120-123° C. (recrystallized from diethyl ether).

후처리

  1. temperaturecooling
  2. concentrationthe reaction solution is concentrated under reduced pressure
  3. additionTo the residue is added ethyl acetate (50 ml)
  4. extractionthe mixture is extracted with a 10% aqueous hydrochloric acid solution (50 ml×2)
  5. extractionthe mixture is extracted with ethyl acetate (50 ml×2)
  6. washThe organic layer is washed with a saturated brine (50 ml×2)
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customThe residue is purified by silica gel column chromatography (eluent: ethyl acetate/methanol)

출처 및 근거

ORD 기록
ord-990723400227454cbfc588de83f45fdd
출처 데이터셋
uspto-grants-2004_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06683186B2

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