Ethanol → (+/-)-1-(3'-Methoxybiphenyl-4-yloxy)-4-(3-pyridyl)-2-butanol

HRID 1600924Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1600924
Cl[CH2:2][CH:3]([OH:12])[CH2:4][CH2:5][C:6]1[CH:7]=[N:8][CH:9]=[CH:10][CH:11]=1.[CH3:13][O:14][C:15]1[CH:16]=[C:17]([C:21]2[CH:26]=[CH:25][C:24]([OH:27])=[CH:23][CH:22]=2)[CH:18]=[CH:19][CH:20]=1.C(O)C.[OH-].[Na+]>CCCCCC>[CH3:13][O:14][C:15]1[CH:16]=[C:17]([C:21]2[CH:26]=[CH:25][C:24]([O:27][CH2:2][CH:3]([OH:12])[CH2:4][CH2:5][C:6]3[CH:7]=[N:8][CH:9]=[CH:10][CH:11]=3)=[CH:23][CH:22]=2)[CH:18]=[CH:19][CH:20]=1

Komponenten

6

Edukt 4

HCID 702EthanolHCID 14798Sodium HydroxideHCID 124650883'-Methoxy(1,1'-biphenyl)-4-olHCID 22465338HCID 22465338, Verbindung

Produkt 1

HCID 21830673(+/-)-1-(3'-Methoxybiphenyl-4-yloxy)-4-(3-pyridyl)-2-butanol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8058HexaneLösungsmittel

Versuchsvorschrift

Prepared according to the method described in Example 24b) from (±)-α-(chloromethyl)-3-pyridinepropanol (1.90 g), 3'-methoxybiphenyl-4-ol (2.05 g), ethanol (40 ml) and aqueous sodium hydroxide (2.1 M, 5 ml). After the reaction was complete it was concentrated under reduced pressure and the residue partitioned between ethyl acetate and water. The combined organic extracts were dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The residue was twice purified by column chromatography over silica eluting with dichloromethane:ethyl acetate as an oil (1.35 g). A white solid was obtained after trituration with ether:hexane.

Aufarbeitung

  1. customPrepared
  2. concentrationwas concentrated under reduced pressure
  3. customthe residue partitioned between ethyl acetate and water
  4. dry with materialThe combined organic extracts were dried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was twice purified by column chromatography over silica eluting with dichloromethane
  8. customA white solid was obtained after trituration with ether

Quellen und Nachweise

ORD-Eintrag
ord-aa9fb16a39c8465fb6fb3fbff1655f53
Quelldatensatz
uspto-grants-1999_11
Patentnummer
US05977105

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