Dimethylformamide → methyl (4E)-4-[[4-[[5-methyl-2-(thiophen-2-ylmethyl)-1,3-oxazol-4-yl]methoxy]phenyl]methoxyimino]-4-phenylbutanoate

HRID 2299835Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2299835
ClCC1N=[C:5]([C:9]2[S:10][CH:11]=[CH:12][CH:13]=2)OC=1C.[OH:14][C:15]1[CH:36]=[CH:35][C:18]([CH2:19][O:20]/[N:21]=[C:22](/[C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)\[CH2:23][CH2:24][C:25]([O:27][CH3:28])=[O:26])=[CH:17][CH:16]=1.C(=O)([O-])[O-].[K+].[K+].[CH3:43][N:44](C)[CH:45]=[O:46].[C:48](OCC)(=O)[CH3:49].[CH3:54]CCCCC>O>[CH3:48][C:49]1[O:46][C:45]([CH2:5][C:9]2[S:10][CH:11]=[CH:12][CH:13]=2)=[N:44][C:43]=1[CH2:54][O:14][C:15]1[CH:16]=[CH:17][C:18]([CH2:19][O:20]/[N:21]=[C:22](/[C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=2)\[CH2:23][CH2:24][C:25]([O:27][CH3:28])=[O:26])=[CH:35][CH:36]=1

Komponenten

7

Edukt 5

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 50764914-(Chloromethyl)-5-methyl-2-(thiophen-2-yl)-1,3-oxazoleHCID 10946929methyl (4E)-4-[(4-hydroxyphenyl)methoxyimino]-4-phenylbutanoateHCID 21226206Ethyl acetate hexane

Produkt 1

HCID 22344623methyl (4E)-4-[[4-[[5-methyl-2-(thiophen-2-ylmethyl)-1,3-oxazol-4-yl]methoxy]phenyl]methoxyimino]-4-phenylbutanoateAusbeute 63 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

A mixture of 4-(chloromethyl)-5-methyl-2-(2-thienyl)oxazole (376 mg), methyl E-4-[(4-hydroxybenzyloxy)imino]-4-phenylbutyrate (500 mg), potassium carbonate (442 mg) and N,N-dimethylformamide (10 ml) was stirred at room temperature for 40 hours. Water was added to the reaction mixture and extracted with ethyl acetate. The ethyl acetate layer was washed with an aqueous saturated solution of sodium chloride, dried (MgSO4) and concentrated. The residue was subjected to silica gel chromatography to obtain methyl E-4-[4-[5-methyl-2-(2-thenyl)-4-oxazolylmethoxy]benzyloxyimino]-4-phenylbutyrate (495 mg, yield 63%) as a colorless oil from an ethyl acetate-hexane (1:5, v/v)-eluted fraction.

Aufarbeitung

  1. extractionextracted with ethyl acetate
  2. washThe ethyl acetate layer was washed with an aqueous saturated solution of sodium chloride
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-58eba6abe52e461992665b882c47fe4f
Quelldatensatz
uspto-grants-2002_12
Patentnummer
US06495581B1

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