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Dichloromethane → 5-(5-Bromopyridin-3-YL)oxazole

HRID 2406707
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2406707
C1(C)C(S([CH2:10][N+:11]#[C-:12])(=O)=O)=CC=CC=1.N12CCCN=C1CCCCC2.ClCCl.[Br:28][C:29]1[CH:30]=[C:31]([CH:35]=[O:36])[CH:32]=[N:33][CH:34]=1>O>[Br:28][C:29]1[CH:30]=[C:31]([C:35]2[O:36][CH:12]=[N:11][CH:10]=2)[CH:32]=[N:33][CH:34]=1
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Komponenten

6

Edukt 4

HCID 6344DichloromethaneHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 27847345-Bromo-3-pyridinecarboxaldehydeHCID 53627694Toluenesulfonylmethyl isocyanide

Produkt 1

HCID 670559205-(5-Bromopyridin-3-YL)oxazoleAusbeute 79,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962
Water
Lösungsmittel

Versuchsvorschrift

Toluenesulfonylmethylisocyanide (126 mg) and 1,8-diazabicyclo[5.4.0]undec-7-ene (122 mg) were added to a dichloromethane (4 ml) solution containing 5-bromo-3-pyridinecarboxaldehyde (100 mg) at room temperature, followed by stirring for 5 hours. Water was added to the reaction solution, followed by extraction with ethyl acetate. The resultant was washed with saturated saline and dried over anhydrous sodium sulfate. Subsequently, the solvent was distilled away under reduced pressure, the obtained residue was purified by silica gel chromatography (n-hexane:ethyl acetate=4:1 to 5:2), and a white solid of 5-(5-bromopyridin-3-yl)oxazole (96 mg) was thus obtained.

Aufarbeitung

  1. extractionfollowed by extraction with ethyl acetate
  2. washThe resultant was washed with saturated saline
  3. dry with materialdried over anhydrous sodium sulfate
  4. distillationSubsequently, the solvent was distilled away under reduced pressure
  5. customthe obtained residue was purified by silica gel chromatography (n-hexane:ethyl acetate=4:1 to 5:2)

Quellen und Nachweise

ORD-Eintrag
ord-11789915ec3742aa93885f967d20ee2b
Quelldatensatz
uspto-grants-2014_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08809371B2

Notizen zur Reaktion

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