Hydrochloric Acid → (8E)-8-phenyl-8-[[4-[(5-phenyl-1,2,4-oxadiazol-3-yl)methoxy]phenyl]methoxyimino]octanoic acid

HRID 2299867Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2299867
O.[OH-].[Li+].[C:4]1(/[C:10](=[N:22]/[O:23][CH2:24][C:25]2[CH:30]=[CH:29][C:28]([O:31][CH2:32][C:33]3[N:37]=[C:36]([C:38]4[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=4)[O:35][N:34]=3)=[CH:27][CH:26]=2)/[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][C:17]([O:19]CC)=[O:18])[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.O.Cl>O1CCCC1.C(O)C>[C:4]1(/[C:10](=[N:22]/[O:23][CH2:24][C:25]2[CH:26]=[CH:27][C:28]([O:31][CH2:32][C:33]3[N:37]=[C:36]([C:38]4[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=4)[O:35][N:34]=3)=[CH:29][CH:30]=2)/[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][C:17]([OH:19])=[O:18])[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 168937Lithium hydroxide, monohydrateHCID 22344614ethyl (8E)-8-phenyl-8-[[4-[(5-phenyl-1,2,4-oxadiazol-3-yl)methoxy]phenyl]methoxyimino]octanoate

Produkt 1

HCID 22344639(8E)-8-phenyl-8-[[4-[(5-phenyl-1,2,4-oxadiazol-3-yl)methoxy]phenyl]methoxyimino]octanoic acidAusbeute 93 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Lithium hydroxide monohydrate (54.9 mg) was added to a solution of ethyl E-8-phenyl-8-[4-(5-phenyl-1,2,4-oxadiazol-3-ylmethoxy)benzyloxyimino]octanoate (236 mg) in tetrahydrofuran (6 ml)-water (4 ml)-ethanol (4 ml) and stirred at room temperature for 4 hours. 1N hydrochloric acid (1.4 ml) 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 recrystallized from ethyl acetate-hexane to obtain E-8-phenyl-8-[4-(5-phenyl-1,2,4-oxadiazol-3-ylmethoxy)benzyloxyimino]octanoic acid (208 mg, yield 93%) as colorless crystals. m.p. 76-77° C.

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
  5. customThe residue was recrystallized from ethyl acetate-hexane

Quellen und Nachweise

ORD-Eintrag
ord-7eb01530886542c4b52380827ed90986
Quelldatensatz
uspto-grants-2002_12
Patentnummer
US06495581B1

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