Dicyclohexylcarbodiimide → 2-[4-(5-[propyloxy]-1-pentyl)phenyl]-5-{[(Z)-3-octenoyl]oxy}pyrimidine

HRID 1728262Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1728262
C1(N=C=NC2CCCCC2)CCCCC1.[CH2:16]([O:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][C:25]1[CH:30]=[CH:29][C:28]([C:31]2[N:36]=[CH:35][C:34]([OH:37])=[CH:33][N:32]=2)=[CH:27][CH:26]=1)[CH2:17][CH3:18].[C:38](O)(=[O:46])[CH2:39]/[CH:40]=[CH:41]\[CH2:42][CH2:43][CH2:44][CH3:45]>CN(C)C1C=CN=CC=1.ClCCl>[CH2:16]([O:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][C:25]1[CH:30]=[CH:29][C:28]([C:31]2[N:36]=[CH:35][C:34]([O:37][C:38](=[O:46])[CH2:39]/[CH:40]=[CH:41]\[CH2:42][CH2:43][CH2:44][CH3:45])=[CH:33][N:32]=2)=[CH:27][CH:26]=1)[CH2:17][CH3:18]

Komponenten

6

Edukt 3

HCID 10868DicyclohexylcarbodiimideHCID 5282715cis-beta-Octenoic acidHCID 190171892-[4-(5-[Propyloxy]-1-pentyl)phenyl]-5-hydroxypyrimidine

Produkt 1

HCID 676342202-[4-(5-[propyloxy]-1-pentyl)phenyl]-5-{[(Z)-3-octenoyl]oxy}pyrimidineAusbeute 83,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

0.8 g of N,N'-dicyclohexylcarbodiimide was added within 5 minutes while stirring to a solution of 1.0 g of 2-[4-(5[propyloxy]-1-pentyl)phenyl]-5-hydroxypyrimidine, 0.4 g of (Z)-3-octenoic acid and 0.05 g of 4-(dimethylamino)pyridine in 30 ml of dichloromethane. The reaction mixture was stirred overnight, then filtered and the filtrate was washed with saturated sodium bicarbonate solution and with water and concentrated. Chromatography of the residue on silica gel with hexane/ethyl acetate (vol. 4:1) and two-fold recrystallization of the thin-layer chromatographically pure fractions gave 1.0 g of 2-[4-(5-[propyloxy]-1-pentyl)phenyl]-5-{[(Z)-3-octenoyl]oxy}pyrimidine.

Aufarbeitung

  1. filtrationfiltered
  2. washthe filtrate was washed with saturated sodium bicarbonate solution and with water
  3. concentrationconcentrated
  4. customChromatography of the residue on silica gel with hexane/ethyl acetate (vol. 4:1) and two-fold recrystallization of the thin-layer chromatographically pure fractions

Quellen und Nachweise

ORD-Eintrag
ord-40373b5c592c4b369fb23c202e4c595d
Quelldatensatz
uspto-grants-1994_07
Patentnummer
US05326497

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