Dimethylformamide → ethyl (8E)-8-[[4-[[2-(furan-2-yl)-5-methyl-1,3-oxazol-4-yl]methoxy]phenyl]methoxyimino]-8-phenyloctanoate

HRID 584472Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 584472
Cl[CH2:2][C:3]1[N:4]=[C:5]([C:9]2[O:10][CH:11]=[CH:12][CH:13]=2)[O:6][C:7]=1[CH3:8].[OH:14][C:15]1[CH:41]=[CH:40][C:18]([CH2:19][O:20]/[N:21]=[C:22](/[C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)\[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][C:29]([O:31][CH2:32][CH3:33])=[O:30])=[CH:17][CH:16]=1.C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>C(OCC)(=O)C.CCCCCC.O>[O:10]1[CH:11]=[CH:12][CH:13]=[C:9]1[C:5]1[O:6][C:7]([CH3:8])=[C:3]([CH2:2][O:14][C:15]2[CH:16]=[CH:17][C:18]([CH2:19][O:20]/[N:21]=[C:22](/[C:34]3[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=3)\[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][C:29]([O:31][CH2:32][CH3:33])=[O:30])=[CH:40][CH:41]=2)[N:4]=1

Komponenten

7

Edukt 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 22344573ethyl (8E)-8-[(4-hydroxyphenyl)methoxyimino]-8-phenyloctanoateHCID 223445824-(Chloromethyl)-2-(furan-2-yl)-5-methyl-1,3-oxazole

Produkt 1

HCID 22344599ethyl (8E)-8-[[4-[[2-(furan-2-yl)-5-methyl-1,3-oxazol-4-yl]methoxy]phenyl]methoxyimino]-8-phenyloctanoateAusbeute 84,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 21226206Ethyl acetate hexaneLösungsmittel

Versuchsvorschrift

A mixture of 4-(chloromethyl)-2-(2-furyl)-5-methyloxazole (340 mg), ethyl E-8-(4-hydroxybenzyloxyimino)-8-phenyloctanoate (600 mg), potassium carbonate (432 mg) and N,N-dimethylformamide (7 ml) was stirred at room temperature for 18 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 ethyl E-8-[4-[2-(2-furyl)-5-methyl-4-oxazolylmethoxy]benzyloxyimino]-8-phenyloctanoate (717 mg, yield 84%) as a colorless oil from an ethyl acetate-hexane (2:9, 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-bd8b9793e94e4e6a80fbc54090190e93
Quelldatensatz
uspto-grants-2005_08
Patentnummer
US06924300B2

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