Dimethylformamide → ethyl 3-[4-[2-(2-furyl)-5-methyl-4-oxazolylmethoxy]-3-methoxybenzyloxy]-1-(4-phenoxybenzyl)-1H-pyrazole-4-carboxylate

HRID 350307

Reaktionsgleichung

Reaktionsgleichung von HRID 350307
[OH:1][C:2]1[C:6]([C:7]([O:9][CH2:10][CH3:11])=[O:8])=[CH:5][N:4]([CH2:12][C:13]2[CH:18]=[CH:17][C:16]([O:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[CH:15][CH:14]=2)[N:3]=1.Cl[CH2:27][C:28]1[CH:46]=[CH:45][C:31]([O:32][CH2:33][C:34]2[N:35]=[C:36]([C:40]3[O:41][CH:42]=[CH:43][CH:44]=3)[O:37][C:38]=2[CH3:39])=[C:30]([O:47][CH3:48])[CH:29]=1.C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>O>[O:41]1[CH:42]=[CH:43][CH:44]=[C:40]1[C:36]1[O:37][C:38]([CH3:39])=[C:34]([CH2:33][O:32][C:31]2[CH:45]=[CH:46][C:28]([CH2:27][O:1][C:2]3[C:6]([C:7]([O:9][CH2:10][CH3:11])=[O:8])=[CH:5][N:4]([CH2:12][C:13]4[CH:18]=[CH:17][C:16]([O:19][C:20]5[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=5)=[CH:15][CH:14]=4)[N:3]=3)=[CH:29][C:30]=2[O:47][CH3:48])[N:35]=1

Komponenten

6

Edukt 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 223445974-(4-Chloromethyl-2-methoxyphenoxymethyl)-2-(2-furyl)-5-methyloxazoleHCID 178469747HCID 178469747, Verbindung

Produkt 1

HCID 69421586ethyl 3-[4-[2-(2-furyl)-5-methyl-4-oxazolylmethoxy]-3-methoxybenzyloxy]-1-(4-phenoxybenzyl)-1H-pyrazole-4-carboxylateAusbeute 94 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

A mixture of ethyl 3-hydroxy-1-(4-phenoxybenzyl)-1H-pyrazole-4-carboxylate (3.00 g), 4-(4-chloromethyl-2-methoxyphenoxymethyl)-2-(2-furyl)-5-methyloxazole (3.00 g), potassium carbonate (2.52 g), and N,N-dimethylformamide (30 ml) was stirred at 80° C. for 8 hours. The reaction mixture was poured into water, and extracted with ethyl acetate. The ethyl acetate layer was washed successively with dilute hydrochloric acid and aqueous sodium chloride solution, dried (MgSO4), and concentrated. The residue was subjected to silica gel column chromatography to obtain ethyl 3-[4-[2-(2-furyl)-5-methyl-4-oxazolylmethoxy]-3-methoxybenzyloxy]-1-(4-phenoxybenzyl)-1H-pyrazole-4-carboxylate (5.30 g, yield: 94%) as colorless crystals from the fraction eluted with ethyl acetate-hexane (1:2, volume ratio). This was recrystallized from ethyl acetate-hexane. Melting point: 98–99° C.

Aufarbeitung

  1. extractionextracted with ethyl acetate
  2. washThe ethyl acetate layer was washed successively with dilute hydrochloric acid and aqueous sodium chloride solution
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-097a6e87607542d5966acfd23458d6af
Quelldatensatz
uspto-grants-2007_02
Patentnummer
US07179823B1

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