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

HRID 1267959
ノート
印刷プレビュー

反応式

HRID 1267959 の反応式
[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
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028
Tetrahydrofuran
溶媒

反応条件

温度
60 °C

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-3e6682ad58dd44c2a5d2f7a95d88d54d
出典データセット
uspto-grants-2003_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06555557B1

反応ノート

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