Dicyclohexylcarbodiimide → HCID 178418275, Verbindung

HRID 1639

Reaktionsgleichung

Reaktionsgleichung von HRID 1639
[CH3:1][Si:2]([CH3:9])([CH3:8])[CH2:3]/[CH:4]=[CH:5]/[CH2:6][OH:7].[OH:10][C:11]1[CH:19]=[CH:18][C:14]([C:15](O)=[O:16])=[CH:13][N:12]=1.C1(N=C=NC2CCCCC2)CCCCC1>CN(C)C1C=CN=CC=1.CN(C)C=O>[OH:10][C:11]1[CH:19]=[CH:18][C:14]([C:15]([O:7][CH2:6]/[CH:5]=[CH:4]/[CH2:3][Si:2]([CH3:9])([CH3:8])[CH3:1])=[O:16])=[CH:13][N:12]=1

Komponenten

6

Edukt 3

HCID 10868DicyclohexylcarbodiimideHCID 21846715(E)-4-(trimethylsilyl)but-2-en-1-olHCID 178418479HCID 178418479, Verbindung

Produkt 1

HCID 178418275HCID 178418275, VerbindungAusbeute 38 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

1.3 g of 4-trimethylsilyl-(E)-but-2-en-1-ol (synthesis described in J. Org. Chem. 1984, 49, 4092), 1.08 g of 6-hydroxy-nicotinic acid and 178 mg of 4-dimethylaminopyridine were placed in succession in 30 ml of abs. dimethylformamide. 1.77 g (1.1 eq.) of dicyclohexylcarbodiimide were added thereto at 0° and the mixture was left to react at room temperature overnight. The separated urea was filtered off, the filtrate was extracted with ethyl acetate, washed twice with H2O, dried over Na2 SO4 and the solvent was removed under reduced pressure. Flash chromatography on SiO2 (hexane/ethyl acetate=1/1) yielded 782 mg of 4-trimethylsilanyl-(E)-but-2-enyl 6-hydroxy-nicotinate as white crystals of m.p. 107°-110° (dec.).

Aufarbeitung

  1. waitat 0° and the mixture was left
  2. customto react at room temperature overnight
  3. filtrationThe separated urea was filtered off
  4. extractionthe filtrate was extracted with ethyl acetate
  5. washwashed twice with H2O
  6. customdried over Na2 SO4
  7. customthe solvent was removed under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-998b94bdae2a4efb8c11261a196e92e3
Quelldatensatz
uspto-grants-1998_03
Patentnummer
US05726191

Verknüpfte Notizen

Wird geladen…