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Ammonium Chloride → 5-Acetylfuro(2,3-c)pyridine

HRID 1251560
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1251560
C(O[C:4]([C:6]1[CH:7]=[C:8]2[CH:14]=[CH:13][O:12][C:9]2=[CH:10][N:11]=1)=[O:5])C.C[Li].[CH2:17](OCC)C.[Cl-].[NH4+]>O1CCCC1>[C:4]([C:6]1[CH:7]=[C:8]2[CH:14]=[CH:13][O:12][C:9]2=[CH:10][N:11]=1)(=[O:5])[CH3:17]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 25517Ammonium ChlorideHCID 11074225Ethyl furo[2,3-c]pyridine-5-carboxylateHCID 178467906HCID 178467906, Verbindung

Produkt 1

HCID 97939025-Acetylfuro(2,3-c)pyridineAusbeute 77 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
-30 °C

Versuchsvorschrift

5-Ethoxycarbonylfuro[2,3-c]pyridine obtained in Example 2(3.82 g, 20.0 mmol) was dissolved in tetrahydrofuran (50 mL) and cooled to −30° C. To the cooled solution, 22.0 mL (22.0 mol) of 1.0 M solution of methyllithium/diethyl ether was added, and the solution was stirred for 2 hours at the same temperature, the reaction mixture was then poured into 100 mL of 5% ammonium chloride aqueous solution which had been cooled on ice, and the product was extracted twice with 100 mL of ethyl acetate. After washing with 100 mL of saturated sodium bicarbonate aqueous solution and 100 mL of saturated saline water, the extract was concentrated to give 3.12 g of crude product. This product was purified by column chromatography on silica gel, giving 2.48 g (77.0% yield) of 5-acetylfuro[2,3-c]pyridine.

Aufarbeitung

  1. temperaturehad been cooled on ice
  2. extractionthe product was extracted twice with 100 mL of ethyl acetate
  3. washAfter washing with 100 mL of saturated sodium bicarbonate aqueous solution and 100 mL of saturated saline water
  4. concentrationthe extract was concentrated
  5. customto give 3.12 g of crude product
  6. customThis product was purified by column chromatography on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-b236aa7b46584658b9e0b1af10856484
Quelldatensatz
uspto-grants-2002_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06342606B2

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