Water → 5-[3-(1-imidazolyl)propyl]-2-[2-[(E)-2-phenylethenyl]-4-oxazolylmethoxy]pyridine

HRID 322445Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 322445
[H-].[Na+].[C:3]1(/[CH:9]=[CH:10]/[C:11]2[O:12][CH:13]=[C:14]([CH2:16][OH:17])[N:15]=2)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.Cl[C:19]1[CH:24]=[CH:23][C:22]([CH2:25][CH2:26][CH2:27][N:28]2[CH:32]=[CH:31][N:30]=[CH:29]2)=[CH:21][N:20]=1.O>CN(C)C=O>[N:28]1([CH2:27][CH2:26][CH2:25][C:22]2[CH:23]=[CH:24][C:19]([O:17][CH2:16][C:14]3[N:15]=[C:11](/[CH:10]=[CH:9]/[C:3]4[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=4)[O:12][CH:13]=3)=[N:20][CH:21]=2)[CH:32]=[CH:31][N:30]=[CH:29]1

Komponenten

6

Edukt 4

HCID 962WaterHCID 24758Sodium hydrideHCID 13657827(E)-(2-Styryloxazol-4-yl)methanolHCID 220095902-Chloro-5-[3-(1-imidazolyl)propyl]pyridine

Produkt 1

HCID 220097425-[3-(1-imidazolyl)propyl]-2-[2-[(E)-2-phenylethenyl]-4-oxazolylmethoxy]pyridineAusbeute 47 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel2×

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

Sodium hydride (oily, 60%, 660 mg) was added to a solution of 2-[(E)-2-phenylethenyl]-4-oxazolylmethanol (3.02 g) in N,N-dimethylformamide (30 ml) and stirred at 90° C. for 30 minutes, to which was added a solution of 2-chloro-5-[3-(1-imidazolyl)propyl]pyridine (1.10 g) in N,N-dimethylformamide (10 ml). The resultant was stirred at 90° C. for 14 hours. The reaction mixture was poured into water, and extracted with ethyl acetate. The ethyl acetate layer was washed with saturated aqueous sodium bicarbonate and brine, dried (MgSO4), and concentrated under reduced pressure. The residue was subjected to a silica gel column chromatography. From the fraction eluted with ethyl acetate-hexane-methanol (10:1:0.5, v/v), crystals of 5-[3-(1-imidazolyl)propyl]-2-[2-[(E)-2-phenylethenyl]-4-oxazolylmethoxy]pyridine (900 mg, 47%) was obtained. Recrystallization ethyl acetate-hexane gave pale brown prisms, mp 120-121° C.

Aufarbeitung

  1. stirringThe resultant was stirred at 90° C. for 14 hours
  2. extractionextracted with ethyl acetate
  3. washThe ethyl acetate layer was washed with saturated aqueous sodium bicarbonate and brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated under reduced pressure
  6. washFrom the fraction eluted with ethyl acetate-hexane-methanol (10:1:0.5

Quellen und Nachweise

ORD-Eintrag
ord-ab516d3c6d474f2da2f6620fcea14b6e
Quelldatensatz
uspto-grants-2001_04
Patentnummer
US06211215B1

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