Triethylene Glycol → 2-(3-Pyridylmethyl)-6-(2-methyl-1,3-dioxolan-2-yl)naphthalene

HRID 35193

Reaktionsgleichung

Reaktionsgleichung von HRID 35193
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]([C:9]2[CH:18]=[CH:17][C:16]3[C:11](=[CH:12][CH:13]=[C:14]([C:19]4([CH3:24])[O:23][CH2:22][CH2:21][O:20]4)[CH:15]=3)[CH:10]=2)=O)[CH:2]=1.C(O)COCCOCCO.NN.[OH-].[K+]>O>[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH2:7][C:9]2[CH:18]=[CH:17][C:16]3[C:11](=[CH:12][CH:13]=[C:14]([C:19]4([CH3:24])[O:20][CH2:21][CH2:22][O:23]4)[CH:15]=3)[CH:10]=2)[CH:2]=1

Komponenten

6

Edukt 4

HCID 8172Triethylene GlycolHCID 9321HydrazineHCID 14797Potassium HydroxideHCID 15612242HCID 15612242, Verbindung

Produkt 1

HCID 156122432-(3-Pyridylmethyl)-6-(2-methyl-1,3-dioxolan-2-yl)naphthaleneAusbeute 62 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
160 °C

Versuchsvorschrift

A mixture of 270 mg of 2-(3-pyridylcarbonyl)-6-(2-methyl-1,3-dioxolan-2-yl)naphthalene, 7 ml of triethylene glycol, 1 ml of anhydrous hydrazine and 500 mg of potassium hydroxide were heated at 160° C. for 30 minutes. The temperature was then raised to 210° C. for 1 hour. The mixture was cooled, poured into water and extracted with methylene chloride. The organic layer was dried over sodium sulfate, the solvent removed under reduced pressure and the residue chromatographed on silica gel to give 160 mg of 2-(3-pyridylmethyl)-6-(2-methyl-1,3dioxolan-2-yl)naphthalene as an oil.

Aufarbeitung

  1. temperatureThe temperature was then raised to 210° C. for 1 hour
  2. temperatureThe mixture was cooled
  3. extractionextracted with methylene chloride
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. customthe solvent removed under reduced pressure
  6. customthe residue chromatographed on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-9b438c38abb14a318e2a01f24f8f5b42
Quelldatensatz
uspto-grants-1988_08
Patentnummer
US04766127

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