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Dimethyl Sulfoxide → 6-Chloro-1-(tetrahydro-pyran-2-yl)-1H-indazole-3-carbaldehyde

HRID 1827460
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1827460
[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([CH2:17][OH:18])=[N:7][N:8]2[CH:11]2[CH2:16][CH2:15][CH2:14][CH2:13][O:12]2)=[CH:4][CH:3]=1.CS(C)=O>CCOC(C)=O.O>[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([CH:17]=[O:18])=[N:7][N:8]2[CH:11]2[CH2:16][CH2:15][CH2:14][CH2:13][O:12]2)=[CH:4][CH:3]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 2

HCID 679Dimethyl SulfoxideHCID 22136538[6-Chloro-1-(tetrahydro-pyran-2-yl)-1H-indazol-3-yl]-methanol

Produkt 1

HCID 221365606-Chloro-1-(tetrahydro-pyran-2-yl)-1H-indazole-3-carbaldehydeAusbeute 98 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A solution of [6-Chloro-1-(tetrahydro-pyran-2-yl)-1H-indazol-3-yl]-methanol (1.75 g, 6.58 mmol), IBX (2.76 g, 9.87 mmol) and DMSO (27 mL) was stirred overnight. The reaction was diluted in EtOAc and water. The layers were separated, and the aqueous was extracted with EtOAc (3×100 mL). The organics were combined and washed with saturated NaCl (100 mL). The organic was dried over MgSO4, filtered, and then concentrated to a solid. The solid was dissolved in CH2Cl2, and filtered. The organic was evaporated to yield the desired product (1.707 g, 92%).

Aufarbeitung

  1. customThe layers were separated
  2. extractionthe aqueous was extracted with EtOAc (3×100 mL)
  3. washwashed with saturated NaCl (100 mL)
  4. dry with materialThe organic was dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated to a solid
  7. dissolutionThe solid was dissolved in CH2Cl2
  8. filtrationfiltered
  9. customThe organic was evaporated

Quellen und Nachweise

ORD-Eintrag
ord-351d824f6538412aa306223e03e08d50
Quelldatensatz
uspto-grants-2006_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07053107B2

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