HCID 54320316, Verbindung → 4'-[(S)-2-methylbutoxycarbonyl]biphenyl-4-ol

HRID 1722611

Reaktionsgleichung

Reaktionsgleichung von HRID 1722611
C([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:20]=[CH:19][C:18]([C:21]([O:23][CH2:24][C@@H:25]([CH3:28])[CH2:26][CH3:27])=[O:22])=[CH:17][CH:16]=2)=[CH:11][CH:10]=1)C1C=CC=CC=1>[Pd].C(OCC)(=O)C>[OH:8][C:9]1[CH:10]=[CH:11][C:12]([C:15]2[CH:20]=[CH:19][C:18]([C:21]([O:23][CH2:24][C@@H:25]([CH3:28])[CH2:26][CH3:27])=[O:22])=[CH:17][CH:16]=2)=[CH:13][CH:14]=1

Komponenten

4

Edukt 1

HCID 54320316HCID 54320316, Verbindung

Produkt 1

HCID 139075384'-[(S)-2-methylbutoxycarbonyl]biphenyl-4-olAusbeute 85,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

In a 125-ml Parr bomb equipped with a magnetic stirrer were placed 960 mg (S)-2-methyl-1-butyl 4-benzyloxy-4'-biphenylcarboxylate, 200 mg 5% palladium on carbon, and 50 ml ethyl acetate. The bomb was purged with argon and pressurized with 500 psi hydrogen. After stirring at room temperature for one day, thin layer chromatographic analysis showed that considerable starting material remained. An additional 200 mg 5% palladium on carbon was carefully added, and the bomb was re-pressurized with 500 psi hydrogen. After stirring for one more day, TLC analysis showed that the reaction was complete. The reaction mixture was filtered through Celite and the solids were washed thoroughly with ethyl acetate. Evaporation of the solvent yielded white crystals which were recrystallized from hexanes at low temperature to yield 0.62 g (85%) of product, mp 111.5°14 113° C., whose structure was confirmed by infrared, nuclear magnetic resonance, and mass spectral analyses, as follows. ##STR28##

Aufarbeitung

  1. customIn a 125-ml Parr bomb equipped with a magnetic stirrer
  2. customThe bomb was purged with argon
  3. additionAn additional 200 mg 5% palladium on carbon was carefully added
  4. stirringAfter stirring for one more day, TLC analysis
  5. filtrationThe reaction mixture was filtered through Celite
  6. washthe solids were washed thoroughly with ethyl acetate
  7. customEvaporation of the solvent
  8. customyielded white crystals which
  9. customwere recrystallized from hexanes at low temperature

Quellen und Nachweise

ORD-Eintrag
ord-1cc1ec1565934424bcfbd4acd35f9bf5
Quelldatensatz
uspto-grants-1989_08
Patentnummer
US04857227

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