Ethanol → Methyl 3-(2,5-dimethyl-1H-pyrrol-1-yl)-6-ethoxy-5-(trifluoromethyl)picolinate

HRID 887866Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 887866
[CH3:1][C:2]1[N:3]([C:8]2[C:9]([C:19]([O:21][CH3:22])=[O:20])=[N:10][C:11]([OH:18])=[C:12]([C:14]([F:17])([F:16])[F:15])[CH:13]=2)[C:4]([CH3:7])=[CH:5][CH:6]=1.[CH3:23][CH2:24]O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O>O1CCOCC1>[CH3:7][C:4]1[N:3]([C:8]2[C:9]([C:19]([O:21][CH3:22])=[O:20])=[N:10][C:11]([O:18][CH2:23][CH3:24])=[C:12]([C:14]([F:15])([F:16])[F:17])[CH:13]=2)[C:2]([CH3:1])=[CH:6][CH:5]=1

Komponenten

6

Edukt 4

HCID 702EthanolHCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylateHCID 178499131Methyl 3-(2,5-dimethyl-1H-pyrrol-1-yl)-6-hydroxy-5-(trifluoromethyl)picolinate

Produkt 1

HCID 67383877Methyl 3-(2,5-dimethyl-1H-pyrrol-1-yl)-6-ethoxy-5-(trifluoromethyl)picolinate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

Methyl 3-(2,5-dimethyl-1H-pyrrol-1-yl)-6-hydroxy-5-(trifluoromethyl)picolinate (62 mg, 0.168 mmol) in 1,4-dioxane (1.5 ml) (dry) was treated with EtOH (0.020 ml, 0.335 mmol) and triphenylphosphine (88 mg, 0.335 mmol) and the solution stirred. DEAD (0.053 ml, 0.335 mmol) was added dropwise and the reaction mixture stirred at room temperature for 2 hours. The solvent was removed in vacuo and purification of the crude product by chromatography on silica eluting with iso-hexane: EtOAc (gradient of 0 to 10% EtOAc) afforded the title compound;

Aufarbeitung

  1. stirringthe reaction mixture stirred at room temperature for 2 hours
  2. customThe solvent was removed in vacuo and purification of the crude product by chromatography on silica eluting with iso-hexane

Quellen und Nachweise

ORD-Eintrag
ord-c6f54a1640fb417e8805381340e20ca8
Quelldatensatz
uspto-grants-2012_08
Patentnummer
US08247436B2

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