Trifluoroacetic acid → 4-propoxy-1H-indazol-5-ol

HRID 1269934Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1269934
FC(F)(F)C(O)=O.[CH2:8]([O:11][C:12]1[C:20]([O:21]C2CCCCO2)=[CH:19][CH:18]=[C:17]2[C:13]=1[CH:14]=[N:15][N:16]2C1CCCCO1)[CH2:9][CH3:10].[OH-].[Na+]>ClCCl>[CH2:8]([O:11][C:12]1[C:20]([OH:21])=[CH:19][CH:18]=[C:17]2[C:13]=1[CH:14]=[N:15][NH:16]2)[CH2:9][CH3:10]

Komponenten

5

Edukt 3

HCID 6422Trifluoroacetic acidHCID 14798Sodium HydroxideHCID 694345664-propoxy-1-tetrahydro-2H-pyran-2-yl-5-(tetrahydro-2H-pyran-2-yloxy)-1H-indazole

Produkt 1

HCID 229337144-propoxy-1H-indazol-5-olAusbeute 74.384,797 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Under a nitrogen atmosphere, trifluoroacetic acid (5.5 ml) was added to a solution of 4-propoxy-1-tetrahydro-2H-pyran-2-yl-5-(tetrahydro-2H-pyran-2-yloxy)-1H-indazole (852.6 mg) in dichloromethane (16.5 ml) at room temperature. After 2.5 hours, the reaction solution was poured onto ice, adjusted to pH 7 with an aqueous sodium hydroxide solution, and then extracted with ethyl acetate. The extract solution was concentrated under reduced pressure and the resulting residue was purified by a silica gel column chromatography (eluent: hexane/ethyl acetate). The residue purified was concentrated under reduced pressure and the resulting residue was washed with diethyl ether/hexane by repulping to obtain 4-propoxy-1H-indazol-5-ol (338.2 g, 80%, two steps).

Aufarbeitung

  1. additionthe reaction solution was poured onto ice
  2. extractionextracted with ethyl acetate
  3. concentrationThe extract solution was concentrated under reduced pressure
  4. customthe resulting residue was purified by a silica gel column chromatography (eluent: hexane/ethyl acetate)
  5. customThe residue purified
  6. concentrationwas concentrated under reduced pressure
  7. washthe resulting residue was washed with diethyl ether/hexane

Quellen und Nachweise

ORD-Eintrag
ord-bc89269cc3b3465ea29b2845a3e92621
Quelldatensatz
uspto-grants-2007_04
Patentnummer
US07199147B2

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