Hydrochloric Acid → HCID 69423290, Verbindung

HRID 349909Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 349909
[H-].[Na+].[C:3]([O:11][CH2:12][CH3:13])(=[O:10])[CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6].I[CH2:15][CH2:16][CH2:17][C:18]1[C:19]([C:44]2[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=2)=[N:20][N:21]([CH2:23][C:24]2[CH:29]=[CH:28][C:27]([O:30][CH2:31][C:32]3[N:33]=[C:34]([C:38]4[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=4)[O:35][C:36]=3[CH3:37])=[CH:26][CH:25]=2)[CH:22]=1.Cl>O1CCCC1>[CH3:37][C:36]1[O:35][C:34]([C:38]2[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=2)=[N:33][C:32]=1[CH2:31][O:30][C:27]1[CH:28]=[CH:29][C:24]([CH2:23][N:21]2[CH:22]=[C:18]([CH2:17][CH2:16][CH2:15][CH:4]([C:5]([O:7][CH2:8][CH3:9])=[O:6])[C:3]([O:11][CH2:12][CH3:13])=[O:10])[C:19]([C:44]3[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=3)=[N:20]2)=[CH:25][CH:26]=1

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 7761Diethyl MalonateHCID 24758Sodium hydrideHCID 23024979HCID 23024979, Verbindung

Produkt 1

HCID 69423290HCID 69423290, VerbindungAusbeute 88,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

Sodium hydride (60%, oily, 476 mg) was added to a solution of diethyl malonate (2.37 g) in tetrahydrofuran (50 ml) at 0° C., and the mixture was stirred for 30 minutes. A solution of 1-iodo-3-[1-[4-(5-methyl-2-phenyl-4-oxazolylmethoxy)benzyl]-3-phenyl-1H-pyrazol-4-yl]propane (1.75 g) in tetrahydrofuran (15 ml) was added dropwise to the above mixture, which was stirred at room temperature for 13 hours. The reaction mixture was acidified with diluted hydrochloric acid, which was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated aqueous sodium chloride solution, dried (MgSO4), and then concentrated. The residue was subjected to silica gel column chromatography, and diethyl 2-[3-[1-[4-(5-methyl-2-phenyl-4-oxazolylmethoxy)benzyl]-3-phenyl-1H-pyrazol-4-yl]propyl]malonate (1.63 g, yield: 88%) was obtained as a colorless oily substance from the fraction eluted with ethyl acetate-hexane (1:2, volume ratio).

Aufarbeitung

  1. stirringwas stirred at room temperature for 13 hours
  2. extractionwas extracted with ethyl acetate
  3. washThe ethyl acetate layer was washed with saturated aqueous sodium chloride solution
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-bd942678f5874e29aa737b36834bd641
Quelldatensatz
uspto-grants-2007_02
Patentnummer
US07179823B1

Notizen zur Reaktion

Wird geladen…