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Triphenylphosphine → HCID 15895874、化合物

HRID 1884574
ノート
印刷プレビュー

反応式

HRID 1884574 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 m), 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)propoxy]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. customthe reaction
  4. concentrationsolution is concentrated under reduced pressure
  5. additionTo the residue is added ethyl acetate (50 m)
  6. extractionthe mixture is extracted with a 10% aqueous hydrochloric acid solution (50 ml×2)
  7. extractionthe mixture is extracted with ethyl acetate (100 ml×2)
  8. washThe organic layer is washed with a saturated brine (50 ml×2)
  9. dry with materialdried over anhydrous magnesium sulfate
  10. concentrationconcentrated under reduced pressure
  11. customThe residue is purified by silica gel column chromatography (eluent: chloroform/methanol)

出典と根拠

ORDレコード
ord-95b3832a648048e5aa6588e19b62f3d3
出典データセット
uspto-grants-2004_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06765095B2

反応ノート

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