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Triphenylphosphine → HCID 15895874、化合物

HRID 1267952
ノート
印刷プレビュー

反応式

HRID 1267952 の反応式
[CH3:1][O:2][C:3]1[CH:4]=[N:5][CH:6]=[C:7]([O:13][CH3:14])[C:8]=1[CH2:9][CH2:10][CH2:11][OH:12].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.[Br:48][C:49]1[CH:50]=[C:51]([CH:60]=[CH:61][CH:62]=1)[O:52][C:53]1[C:58](O)=[CH:57][CH:56]=[CH:55][N:54]=1>C1COCC1>[Br:48][C:49]1[CH:50]=[C:51]([CH:60]=[CH:61][CH:62]=1)[O:52][C:53]1[C:58]([O:12][CH2:11][CH2:10][CH2:9][C:8]2[C:3]([O:2][CH3:1])=[CH:4][N:5]=[CH:6][C:7]=2[O:13][CH3:14])=[CH:57][CH:56]=[CH:55][N:54]=1
参加物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 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 12149155HCID 12149155、化合物HCID 235062572-(3-Bromophenoxy)-3-pyridinol

生成物 1

HCID 15895874HCID 15895874、化合物

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

3-(3,5-Dimethoxypyridin-4-yl)-1-propanol (0.60 g, 3.0 mmol) obtained in Example 1 and triphenylphosphine (1.18 g, 4.5 mmol) are dissolved in THF (30 ml), and thereto are successively added with stirring diisopropyl azodicarboxylate (0.78 g, 3.9 mmol) and 2-(3-bromophenoxy)-3-pyridinol (1.04 g, 3.9 mmol) obtained in Reference Example 11 under ice-cooling. The mixture is stirred at room temperature for 30 minutes, 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 (100 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: chloroform/methanol) to give 2-(3-bromophenoxy)-3-[3-(3,5-dimethoxypyridin-4-yl)propoxyl]pyridine, which is further treated with fumaric acid to give the title compound (1.26 g), m.p. 106-154° C.

後処理

  1. customobtained in Reference Example 11 under ice-
  2. temperaturecooling
  3. concentrationthe reaction solution is concentrated under reduced pressure
  4. additionTo the residue is added ethyl acetate (50 ml)
  5. extractionthe mixture is extracted with a 10% aqueous hydrochloric acid solution (50 ml×2)
  6. extractionthe mixture is extracted with ethyl acetate (100 ml×2)
  7. washThe organic layer is washed with a saturated brine (50 ml×2)
  8. dry with materialdried over anhydrous magnesium sulfate
  9. concentrationconcentrated under reduced pressure
  10. customThe residue is purified by silica gel column chromatography (eluent: chloroform/methanol)

出典と根拠

ORDレコード
ord-54ac8755b6f9468bbe5e95b62631cae2
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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