Triacetoxyperiodinane → 1-allyl-4-(2,2,2-trifluoro-acetyl)-1H-pyrrole-2-carbonitrile

HRID 244441Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 244441
[CH2:1]([N:4]1[CH:8]=[C:7]([CH:9]([OH:14])[C:10]([F:13])([F:12])[F:11])[CH:6]=[C:5]1[C:15]#[N:16])[CH:2]=[CH2:3].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.C([O-])(O)=O.[Na+]>C(Cl)Cl>[CH2:1]([N:4]1[CH:8]=[C:7]([C:9](=[O:14])[C:10]([F:13])([F:11])[F:12])[CH:6]=[C:5]1[C:15]#[N:16])[CH:2]=[CH2:3]

Komponenten

5

Edukt 3

HCID 159087TriacetoxyperiodinaneHCID 516892Sodium BicarbonateHCID 594372371-allyl-4-(2,2,2-trifluoro-1-hydroxyethyl)-1H-pyrrole-2-carbonitrile

Produkt 1

HCID 594372991-allyl-4-(2,2,2-trifluoro-acetyl)-1H-pyrrole-2-carbonitrile

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

To a room temperature solution of 1-allyl-4-(2,2,2-trifluoro-1-hydroxyethyl)-1H-pyrrole-2-carbonitrile (1.6 g, 7 mmol, 1 equiv.) in 50 mL of CH2Cl2 was added Dess-Martin periodinane (3.6 g, 8.3 mmol, 1.2 equiv). After 3 hours, the reaction was diluted with CH2Cl2 and made basic with saturated NaHCO3. The organic layer was separated and the aqueous extracted with CH2Cl2. The combined organic layers were dried, filtered, and concentrated in vacuo. The residue was purified by flash chromatography using EtOAc-hexanes (0-15% gradient) to provide 1-allyl-4-(2,2,2-trifluoro-acetyl)-1H-pyrrole-2-carbonitrile which was used without further purification.

Aufarbeitung

  1. customThe organic layer was separated
  2. extractionthe aqueous extracted with CH2Cl2
  3. customThe combined organic layers were dried
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by flash chromatography

Quellen und Nachweise

ORD-Eintrag
ord-d4b6632dc2bf46299091ac700277130b
Quelldatensatz
uspto-grants-2014_02
Patentnummer
US08658637B2

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