Sodium hydride → (2S)-1-(3'-Cyanobiphenyl-4-yloxy)-4-(3-pyridyl)-2-butanol

HRID 1600916Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1600916
C1(C)C=CC(S([O:10][CH2:11][C@@H:12]([O:21][Si](C(C)(C)C)(C)C)[CH2:13][CH2:14][C:15]2[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=2)(=O)=O)=CC=1.[H-].[Na+].[C:32]([C:34]1[CH:35]=[C:36]([C:40]2[CH:45]=[CH:44][C:43](O)=[CH:42][CH:41]=2)[CH:37]=[CH:38][CH:39]=1)#[N:33].[F-].C([N+](CCCC)(CCCC)CCCC)CCC>CN(C)C=O.O1CCCC1.[Cl-].[Na+].O>[C:32]([C:34]1[CH:35]=[C:36]([C:40]2[CH:45]=[CH:44][C:43]([O:10][CH2:11][C@@H:12]([OH:21])[CH2:13][CH2:14][C:15]3[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=3)=[CH:42][CH:41]=2)[CH:37]=[CH:38][CH:39]=1)#[N:33]

Komponenten

8

Edukt 4

HCID 24758Sodium hydrideHCID 2724141Tetrabutylammonium FluorideHCID 37790963-(4-Hydroxyphenyl)benzonitrileHCID 57045765(2S)-2-(tert-Butyldimethylsilyloxy)-4-(3-pyridyl)-1-butyl para-toluenesulfonate

Produkt 1

HCID 57040847(2S)-1-(3'-Cyanobiphenyl-4-yloxy)-4-(3-pyridyl)-2-butanolAusbeute 60,5 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 6228DimethylformamideLösungsmittelHCID 8028TetrahydrofuranLösungsmittelHCID 57417360Sodium chloride; waterLösungsmittel

Versuchsvorschrift

Prepared according to the method described in Example 26e) from (2S)-2-(tert-butyldimethylsilyloxy)-4-(3-pyridyl)-1-butyl para-toluenesulfonate (0.46 g, Example 26d)), sodium hydride (60%, 0.056 g) and 4-(3-cyanophenyl)phenol (0.273 g) in dimethylformamide (5 ml). The adduct was dissolved in tetrahydrofuran (10 ml) and tetrabutylammonium fluoride (0.522 g) was added. The reaction was stirred at ambient temperature for 1 hour and was then poured into brine and extracted with ethyl acetate. The combined organic extracts were dried over anhydrous magnesium sulfate, filtered, concentrated under reduced pressure. The residue obtained was purified by column chromatography over silica eluting with ethyl acetate to give the title compound as a solid (0.22 g).

Aufarbeitung

  1. customPrepared
  2. extractionextracted with ethyl acetate
  3. dry with materialThe combined organic extracts were dried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue obtained
  7. customwas purified by column chromatography over silica eluting with ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-cfe1f42e71b24896b42bd55b55c55970
Quelldatensatz
uspto-grants-1999_11
Patentnummer
US05977105

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