Water → HCID 70197198, Verbindung

HRID 1419855Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1419855
[Na].[C:2]([CH2:4][C:5]1[CH:10]=[C:9]([CH3:11])[CH:8]=[CH:7][N:6]=1)#[N:3].[Cl:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[CH:19](CO)[C:20]([OH:22])=O.[OH2:25]>CO>[Cl:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[CH:19]1[C:20](=[O:22])[C:4]([C:5]2[CH:10]=[C:9]([CH3:11])[CH:8]=[CH:7][N:6]=2)=[C:2]([NH2:3])[O:25]1

Komponenten

6

Edukt 4

HCID 962WaterHCID 5360545Sodium2×HCID 12812206(4-Methylpyridin-2-yl)acetonitrileHCID 53970006HCID 53970006, Verbindung

Produkt 1

HCID 70197198HCID 70197198, VerbindungAusbeute 28 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

Sodium (0.35 g, 15.2 mmol) was added in methanol (8 ml) and stirred at room temperature under nitrogen atomsphere till complete dissolution of sodium, and then 2-cyanomethyl-4-methylpyridine (1.10 g, 8.51 mmol) and 2-(o-chlorophenyl)2-hydroxymethylacetic acid (1.78 g, 1.35 mmol) were slowly added. After refluxing for 2 hours with stirring the solution was cooled with a small amount of water and concentrated under the reduced pressure. The residue was extracted with methylene chloride and the combined organic layers were dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure to get crude product. The residue was separated and purified by column-chromatography over silica gel to obtain the desired product (0.54 g, yield=28%).

Aufarbeitung

  1. temperatureAfter refluxing for 2 hours
  2. concentrationconcentrated under the reduced pressure
  3. extractionThe residue was extracted with methylene chloride
  4. dry with materialthe combined organic layers were dried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customto get crude product
  8. customThe residue was separated
  9. custompurified by column-chromatography over silica gel

Quellen und Nachweise

ORD-Eintrag
ord-f7b3f025afa041d9be10309080f63d0f
Quelldatensatz
uspto-grants-1999_03
Patentnummer
US05889027

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