Triphenylphosphine → 5-(3-((4-Acetyl-3-hydroxy-2-methylphenoxy)methyl)phenylthio) picolinonitrile

HRID 2267062Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2267062
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C.[OH:34][CH2:35][C:36]1[CH:37]=[C:38]([S:42][C:43]2[CH:44]=[CH:45][C:46]([C:49]#[N:50])=[N:47][CH:48]=2)[CH:39]=[CH:40][CH:41]=1.[OH:51][C:52]1[C:57]([CH3:58])=[C:56](O)[CH:55]=[CH:54][C:53]=1[C:60](=[O:62])[CH3:61]>C1COCC1.C(OCC)(=O)C>[C:60]([C:53]1[CH:54]=[CH:55][C:56]([O:34][CH2:35][C:36]2[CH:37]=[C:38]([S:42][C:43]3[CH:44]=[CH:45][C:46]([C:49]#[N:50])=[N:47][CH:48]=3)[CH:39]=[CH:40][CH:41]=2)=[C:57]([CH3:58])[C:52]=1[OH:51])(=[O:62])[CH3:61]

Komponenten

7

Edukt 4

HCID 11776TriphenylphosphineHCID 5921391-(2,4-Dihydroxy-3-methylphenyl)ethan-1-oneHCID 5363146Diisopropyl azodicarboxylateHCID 68535288HCID 68535288, Verbindung

Produkt 1

HCID 595995135-(3-((4-Acetyl-3-hydroxy-2-methylphenoxy)methyl)phenylthio) picolinonitrileAusbeute 73 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

Add triphenylphosphine (1.84 g, 7.02 mmol) and diisopropylazodicarboxylate (1.42 g, 7.02 mmol) to a solution of 5-(3-(hydroxymethyl)phenylthio)picolinonitrile (1.70 g, 7.02 mmol) and 1-(2,4-dihydroxy-3-methylphenyl)ethanone (1.17 g, 7.02 mmol) in THF (35.1 mL). Stir overnight. Dilute with ethyl acetate. Wash the mixture with water and brine. Dry, filter and concentrate to afford the title compound (2.00 g, 73%). Use as is. MS (APCI-neg) m/z (rel intensity): 390 (M+H, 100%).

Aufarbeitung

  1. washWash the mixture with water and brine
  2. customDry
  3. filtrationfilter
  4. concentrationconcentrate

Quellen und Nachweise

ORD-Eintrag
ord-ef27bc10ad9744f690a660c7106fb1fc
Quelldatensatz
uspto-grants-2010_12
Patentnummer
US07858646B2

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