StartseiteMCPWorkbenchSkills
StartseiteWorkbenchBenachrichtigungenMein Bereich
llms.txt · MCP-AnleitungDatenschutz · Nutzungsbedingungen · Supportv1.8.0
  1. Startseite
  2. /Reaktion

4-Hydroxybiphenyl → (2S)-4-(3-Pyridyl)-1-[(4-phenyl)phenoxy]-butan-2-ol

HRID 1600904
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1600904
[C:1]1([C:7]2[CH:12]=[CH:11][C:10]([OH:13])=[CH:9][CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].C1(C)C=CC(S(O[CH2:26][C@@H:27]([O:36][Si](C(C)(C)C)(C)C)[CH2:28][CH2:29][C:30]2[CH:31]=[N:32][CH:33]=[CH:34][CH:35]=2)(=O)=O)=CC=1.F.C(=O)([O-])O.[Na+]>CN(C)C=O.C(#N)C.O>[N:32]1[CH:33]=[CH:34][CH:35]=[C:30]([CH2:29][CH2:28][C@H:27]([OH:36])[CH2:26][O:13][C:10]2[CH:9]=[CH:8][C:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)=[CH:12][CH:11]=2)[CH:31]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

9

Edukt 5

HCID 71034-HydroxybiphenylHCID 14917Hydrofluoric AcidHCID 24758Sodium hydrideHCID 516892Sodium BicarbonateHCID 57045765(2S)-2-(tert-Butyldimethylsilyloxy)-4-(3-pyridyl)-1-butyl para-toluenesulfonate

Produkt 1

HCID 57091781
(2S)-4-(3-Pyridyl)-1-[(4-phenyl)phenoxy]-butan-2-ol
Ausbeute 70,5 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittelHCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

Solid 4-phenylphenol (0.43 g) was added to a stirred suspension of sodium hydride (60%, 0.096 g) in dimethylformamide (5 ml) and the resulting solution stirred for 30 minutes. (2S)-2-(tert-Butyldimethylsilyloxy)-4-(3-pyridyl)-1-butyl para-toluenesulfonate (0.84 g) was added and the mixture stirred at 60° C. for 2 hours. After cooling the mixture was poured into water (50 ml) and extracted with ethyl acetate. The combined organic extracts were dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The residue obtained was dissolved in acetonitrile (10 ml) and hydrofluoric acid (40%; 1 ml) was added. The mixture was stirred for 1 hour and then poured into a solution of saturated aqueous sodium hydrogencarbonate. The mixture was extracted with ethyl acetate and the combined organic extracts were dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure to give the title compound (0.434 g) as a solid that was recrystallised from ethyl acetate:hexane.

Aufarbeitung

  1. stirringthe mixture stirred at 60° C. for 2 hours
  2. temperatureAfter cooling the mixture
  3. extractionextracted with ethyl acetate
  4. dry with materialThe combined organic extracts were dried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue obtained
  8. stirringThe mixture was stirred for 1 hour
  9. extractionThe mixture was extracted with ethyl acetate
  10. dry with materialthe combined organic extracts were dried over anhydrous magnesium sulfate
  11. filtrationfiltered
  12. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-b6366b00aed540378edb6c0ed1db6fe7
Quelldatensatz
uspto-grants-1999_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05977105

Notizen zur Reaktion

Wird geladen…

Auf dieser SeiteKomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion