Hydrochloric Acid → 1-(3-{[3-methoxy-4-(5-methyl-2-phenyl-1,3-oxazol-4-ylmethoxy)benzyl]oxy}-1-methyl-1H-pyrazol-4-yl)ethanone

HRID 2221954Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2221954
CON(C)[C:4]([C:6]1[C:7]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][C:17]([O:20][CH2:21][C:22]3[N:23]=[C:24]([C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=4)[O:25][C:26]=3[CH3:27])=[C:16]([O:34][CH3:35])[CH:15]=2)=[N:8][N:9]([CH3:11])[CH:10]=1)=[O:5].[CH3:37][Mg]Br.Cl>O1CCCC1>[CH3:35][O:34][C:16]1[CH:15]=[C:14]([CH:19]=[CH:18][C:17]=1[O:20][CH2:21][C:22]1[N:23]=[C:24]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[O:25][C:26]=1[CH3:27])[CH2:13][O:12][C:7]1[C:6]([C:4](=[O:5])[CH3:37])=[CH:10][N:9]([CH3:11])[N:8]=1

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 23076606HCID 23076606, VerbindungHCID 178418573HCID 178418573, Verbindung

Produkt 1

HCID 692163781-(3-{[3-methoxy-4-(5-methyl-2-phenyl-1,3-oxazol-4-ylmethoxy)benzyl]oxy}-1-methyl-1H-pyrazol-4-yl)ethanoneAusbeute 97 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of N-methoxy-N-methyl-3-{[3-methoxy-4-(5-methyl-2-phenyl-1,3-oxazol-4-ylmethoxy)benzyl]oxy}-1-methyl-1H-pyrazole-4-carboxamide (3.00 g) in tetrahydrofuran (30 mL) was slowly added methylmagnesium bromide (1.0 M tetrahydrofuran solution, 15 mL) at 0° C., and the mixture was stirred at room temperature for 2 hrs. The reaction mixture was poured into dilute hydrochloric acid, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated to give 1-(3-{[3-methoxy-4-(5-methyl-2-phenyl-1,3-oxazol-4-ylmethoxy)benzyl]oxy}-1-methyl-1H-pyrazol-4-yl)ethanone (2.65 g, yield 97%) as colorless crystals. The crystals were recrystallized from acetone-hexane. melting point: 170-171° C.

Aufarbeitung

  1. customat 0° C.
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe ethyl acetate layer was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-ed18bd96434f4b609405958185186572
Quelldatensatz
uspto-grants-2008_05
Patentnummer
US07368578B2

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