Triphenylphosphine → HCID 117770232, Verbindung

HRID 1526380Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1526380
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][NH:6][C:5](=[O:9])[C:4]=1[C:10]#[N:11].[S:12]1[CH2:17][CH2:16][CH:15](O)[CH2:14][CH2:13]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>C(=O)([O-])O.[Na+].O1CCCC1>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][N:6]([CH:15]2[CH2:16][CH2:17][S:12][CH2:13][CH2:14]2)[C:5](=[O:9])[C:4]=1[C:10]#[N:11]

Komponenten

7

Edukt 4

HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 576296Tetrahydro-2H-thiopyran-4-olHCID 27867023-Pyridinecarbonitrile, 1,2-dihydro-4-methoxy-2-oxo-

Produkt 1

HCID 117770232HCID 117770232, VerbindungAusbeute 19,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 516892Sodium BicarbonateLösungsmittel

Versuchsvorschrift

To a mixture of 4-methoxy-2-oxo-1,2-dihydropyridine-3-carbonitrile (1.00 g), tetrahydro-2H-thiopyran-4-ol (1.18 g), triphenylphosphine (2.62 g) and tetrahydrofuran (30 mL) was added dropwise diisopropyl azodicarboxylate (2.02 g) at room temperature under nitrogen atmosphere, and the mixture was stirred overnight at room temperature. The reaction mixture was diluted with saturated aqueous sodium hydrogen carbonate solution, and the mixture was extracted twice with ethyl acetate. The extracts were combined, washed with saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (320 mg).

Aufarbeitung

  1. extractionthe mixture was extracted twice with ethyl acetate
  2. washwashed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

Quellen und Nachweise

ORD-Eintrag
ord-3ee9519ebdaa45ee82d64eab6a70de62
Quelldatensatz
uspto-grants-2015_07
Patentnummer
US09085578B2

Notizen zur Reaktion

Wird geladen…