Triethylamine → 2-(5-Formyl-isoxazol-3-yl)-pyridine

HRID 2407708Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2407708
N1C=CC=CC=1.S(=O)(=O)=O.[N:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[C:17]1[CH:21]=[C:20]([CH2:22][OH:23])[O:19][N:18]=1.C(N(CC)CC)C>CS(C)=O.ClCCl.C(OCC)(=O)C>[N:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[C:17]1[CH:21]=[C:20]([CH:22]=[O:23])[O:19][N:18]=1

Komponenten

7

Edukt 3

HCID 8471TriethylamineHCID 168533Sulfur trioxide-pyridineHCID 6865423-(2-Pyridinyl)-5-isoxazolemethanol

Produkt 1

HCID 226312282-(5-Formyl-isoxazol-3-yl)-pyridineAusbeute 18 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 679Dimethyl SulfoxideLösungsmittelHCID 6344DichloromethaneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

Sulfur trioxide pyridine (10.0 g, 62.8 mmol) was dissolved in dimethylsulfoxide (50 mL) and cooled to near 0° C. A solution of the compound prepared in Example 124 (5.05 g, 28.7 mmol) and triethylamine (16.0 mL, 115 mmol) in dichloromethane (40 mL) was added to the solution over 45 minutes. The reaction was warmed to room temperature and stirred overnight. The reaction was diluted with ethyl acetate and washed with sodium hydrogen carbonate aqueous solution. The organic phase was washed with water and dried over magnesium sulfate. The crude mixture was purified by column chromatography using an eluant of 1 to 3% ethyl acetate/dichloromethane to provide the title compound (0.90 g) with the following physical data.

Aufarbeitung

  1. temperaturecooled
  2. customto near 0° C
  3. washwashed with sodium hydrogen carbonate aqueous solution
  4. washThe organic phase was washed with water
  5. dry with materialdried over magnesium sulfate
  6. customThe crude mixture was purified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-13a27517018148cda4c13d12c0b4ee0e
Quelldatensatz
uspto-grants-2014_08
Patentnummer
US08809538B2

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