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Ethanol → Ethyl 3-fluoro-5-hydroxypicolinate

HRID 2277300
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2277300
[Si]([O:18][C:19]1[CH:20]=[C:21]([F:26])[C:22](Cl)=[N:23][CH:24]=1)(C(C)(C)C)(C1C=CC=CC=1)C1C=CC=CC=1.C(N(CC)CC)C.[CH2:34]([OH:36])[CH3:35].CN([CH:40]=[O:41])C>[Pd](Cl)Cl.C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2].O>[F:26][C:21]1[C:22]([C:40]([O:36][CH2:34][CH3:35])=[O:41])=[N:23][CH:24]=[C:19]([OH:18])[CH:20]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 702EthanolHCID 6228DimethylformamideHCID 8471TriethylamineHCID 867313815-((Tert-butyl(diphenyl)silyl)oxy)-2-chloro-3-fluoropyridine

Produkt 1

HCID 86731382Ethyl 3-fluoro-5-hydroxypicolinate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 44119782
Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)
Katalysator
HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

A mixture of 5-((tert-butyl(diphenyl)silyl)oxy)-2-chloro-3-fluoropyridine (29.5 g), 1,1′-bis(diphenylphosphino)ferrocene-palladium(II) dichloride (5.59 g), triethylamine (10.7 mL), ethanol (300 mL) and DMF (300 mL) was stirred overnight at 80° C. under a carbon monoxide atmosphere. To the reaction mixture was added water, and the mixture was extracted with ethyl acetate. The combined organic layer were 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 (hexane/ethyl acetate) to give the title compound (30.8 g) as a mixture with DMF.

Aufarbeitung

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe combined organic layer were washed 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 (hexane/ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-6e9241dba6cc43e586c897bb30a657cd
Quelldatensatz
uspto-grants-2015_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09133129B2

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