Dimethylformamide → HCID 23024929, Verbindung

HRID 350086Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 350086
[H-].[Na+].[N:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[C:10]([C:14]([O:16][CH2:17][CH3:18])=[O:15])=[CH:11][NH:12][CH:13]=1.Cl[CH2:20][C:21]1[CH:40]=[CH:39][C:24]([O:25][CH2:26][C:27]2[N:28]=[C:29]([C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)[O:30][C:31]=2[CH3:32])=[CH:23][CH:22]=1.CN(C)C=O>O>[CH3:32][C:31]1[O:30][C:29]([C:33]2[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=2)=[N:28][C:27]=1[CH2:26][O:25][C:24]1[CH:23]=[CH:22][C:21]([CH2:20][N:12]2[CH:13]=[C:9]([C:4]3[CH:5]=[CH:6][CH:7]=[CH:8][N:3]=3)[C:10]([C:14]([O:16][CH2:17][CH3:18])=[O:15])=[CH:11]2)=[CH:40][CH:39]=1

Komponenten

6

Edukt 4

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 109469404-(4-Chloromethylphenoxy)methyl-5-methyl-2-phenyloxazoleHCID 23024926Ethyl 4-(pyridin-2-yl)-1H-pyrrole-3-carboxylate

Produkt 1

HCID 23024929HCID 23024929, VerbindungAusbeute 97 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

Sodium hydride (60%, oily, 0.22 g) was added to a mixture of ethyl 4-(2-pyridyl)pyrrole-3-carboxylate (1.10 g), 4-(4-chlorometylphenoxymethyl)-5-methyl-2-phenyloxazole (1.83 g) and N,N-dimethylformamide (25 ml) at 0° C., and the mixture was stirred for 1 hour. The reaction mixture was poured into water, which was extracted with ethyl acetate. The ethyl acetate layer was washed with water, then with saturated aqueous sodium chloride solution, dried (MgSO4), and concentrated. The residue was subjected to silica gel column chromatograpy, and ethyl 1-[4-(5-methyl-2-phenyl-4-oxazolylmethoxy)benzyl]-4-(2-pyridyl)pyrrole-3-carboxylate (2.43 g, yield: 97%) was obtained as an oily substance from the fraction eluted with tetrahydrofuran-hexane (1:1, volume ratio).

Aufarbeitung

  1. extractionwas extracted with ethyl acetate
  2. washThe ethyl acetate layer was washed with water
  3. dry with materialwith saturated aqueous sodium chloride solution, dried (MgSO4)
  4. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-52b14dd80e2f435f94dc654ce1e2df86
Quelldatensatz
uspto-grants-2007_02
Patentnummer
US07179823B1

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