Benzyl 2'-(3-tert-butoxy-2,2-dimethyl-3-oxopropoxy)-3-fluorobiphenyl-4-carboxylate → 2'-(3-Tert-butoxy-2,2-dimethyl-3-oxopropoxy)-3-fluorobiphenyl-4-carboxylic acid

HRID 1026559Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1026559
[C:1]([O:5][C:6](=[O:35])[C:7]([CH3:34])([CH3:33])[CH2:8][O:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[C:16]1[CH:21]=[CH:20][C:19]([C:22]([O:24]CC2C=CC=CC=2)=[O:23])=[C:18]([F:32])[CH:17]=1)([CH3:4])([CH3:3])[CH3:2]>O.O1CCCC1.[C].[Pd]>[C:1]([O:5][C:6](=[O:35])[C:7]([CH3:34])([CH3:33])[CH2:8][O:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[C:16]1[CH:21]=[CH:20][C:19]([C:22]([OH:24])=[O:23])=[C:18]([F:32])[CH:17]=1)([CH3:4])([CH3:2])[CH3:3]

Komponenten

5

Edukt 1

HCID 68006312Benzyl 2'-(3-tert-butoxy-2,2-dimethyl-3-oxopropoxy)-3-fluorobiphenyl-4-carboxylate

Produkt 1

HCID 680062602'-(3-Tert-butoxy-2,2-dimethyl-3-oxopropoxy)-3-fluorobiphenyl-4-carboxylic acidAusbeute 68,8 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418390HCID 178418390, VerbindungKatalysatorHCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a mixed solvent solution of benzyl 2′-(3-tert-butoxy-2,2-dimethyl-3-oxopropoxy)-3-fluorobiphenyl-4-carboxylate (15.0 g) in water (75 ml) and tetrahydrofuran (300 ml) was added 10% palladium carbon (4.50 g), followed by stirring at room temperature for 7 hours under a hydrogen atmosphere. The reaction solution was filtered through Celite, and washed with methanol, and then the filtrate was concentrated under reduced pressure. The residue was dissolved in dichloromethane, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to afford 2′-(3-tert-butoxy-2,2-dimethyl-3-oxopropoxy)-3-fluorobiphenyl-4-carboxylic acid (8.38 g).

Aufarbeitung

  1. filtrationThe reaction solution was filtered through Celite
  2. washwashed with methanol
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. dissolutionThe residue was dissolved in dichloromethane
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-1d0a02c745034adabb597dd5ddbd160a
Quelldatensatz
uspto-grants-2014_05
Patentnummer
US08729095B2

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