Nitrogen → 7-(4-Fluorophenyl)-5-oxo-5,7-dihydrofuro[3,4-b]pyridine

HRID 1382195

Reaktionsgleichung

Reaktionsgleichung von HRID 1382195
[C:1]([C:5]1[C:6]([C:11]([OH:13])=O)=[N:7][CH:8]=[CH:9][CH:10]=1)([O:3]C)=O.[F:14][C:15]1[CH:22]=[CH:21][C:18](C=O)=[CH:17][CH:16]=1.N#N>CC1C=CC(C(C)C)=CC=1>[F:14][C:15]1[CH:22]=[CH:21][C:18]([CH:11]2[C:6]3=[N:7][CH:8]=[CH:9][CH:10]=[C:5]3[C:1](=[O:3])[O:13]2)=[CH:17][CH:16]=1

Komponenten

5

Edukt 3

HCID 947NitrogenHCID 680234-FluorobenzaldehydeHCID 2906973-(Methoxycarbonyl)pyridine-2-carboxylic acid

Produkt 1

HCID 145812977-(4-Fluorophenyl)-5-oxo-5,7-dihydrofuro[3,4-b]pyridine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 7463P-CymeneLösungsmittel

Versuchsvorschrift

A suspension of 3-carbomethoxypicolinic acid (15.0 g, 0.083 mol) and 4-fluorobenzaldehyde (90.8 g. 0.732 mol) in 250 mL of p-cymene is heated to reflux under a stream of N2 for 16 hours. The mixture is then allowed to cool to room temperature, filtered and the filtrate distilled in vacuo to remove p-cymene. A solution of the crude residue in CH2Cl2 is chromatographed on silica gel (using Et2O-hexane (2:1) as the eluent). Recrystallization from hexane-EtOAc gives pure 7-(4-fluorophenyl)-5-oxo-5,7-dihydrofuro[3,4-b]pyridine. M.P. 116°-117.5° C.

Aufarbeitung

  1. temperatureis heated
  2. filtrationfiltered
  3. distillationthe filtrate distilled in vacuo
  4. customto remove p-cymene
  5. customA solution of the crude residue in CH2Cl2 is chromatographed on silica gel (
  6. customRecrystallization from hexane-EtOAc

Quellen und Nachweise

ORD-Eintrag
ord-d0750fe4bba1443fb6b24b7d1c769a09
Quelldatensatz
uspto-grants-1989_02
Patentnummer
US04806535

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