Acetic Acid → HCID 22344558, Verbindung

HRID 2299860Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2299860
[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[N:4][C:3]=1[CH2:13][O:14][C:15]1[CH:23]=[CH:22][C:18]([CH2:19][O:20][NH2:21])=[CH:17][CH:16]=1.[Cl:24][C:25]1[CH:30]=[CH:29][C:28]([C:31](=O)[CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][C:38]([OH:40])=[O:39])=[CH:27][CH:26]=1.[C:42](O)(=O)C.C([O-])(=O)C.[Na+]>C(OCC)(=O)C.CCCCCC.O.CO>[Cl:24][C:25]1[CH:30]=[CH:29][C:28](/[C:31](=[N:21]/[O:20][CH2:19][C:18]2[CH:17]=[CH:16][C:15]([O:14][CH2:13][C:3]3[N:4]=[C:5]([C:7]4[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=4)[O:6][C:2]=3[CH3:1])=[CH:23][CH:22]=2)/[CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][C:38]([O:40][CH3:42])=[O:39])=[CH:27][CH:26]=1

Komponenten

8

Edukt 4

HCID 176Acetic AcidHCID 517045Sodium AcetateHCID 223445934-(5-Methyl-2-phenyl4-oxazolylmethoxy)benzyloxyamineHCID 223446108-(4-Chlorophenyl)-8-oxooctanoic acid

Produkt 1

HCID 22344558HCID 22344558, VerbindungAusbeute 75 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 887MethanolLösungsmittelHCID 962WaterLösungsmittelHCID 21226206Ethyl acetate hexaneLösungsmittel

Versuchsvorschrift

After a mixture of 4-(5-methyl-2-phenyl-4-oxazolylmethoxy)benzyloxyamine (600 mg), 8-(4-chlorophenyl)-8-oxooctanoic acid (546 mg), acetic acid (0.331 ml), sodium acetate (317 mg) and methanol (20 ml) was heated to reflux for 18 hours, the mixture was cooled to room temperature. 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-8-(4-chlorophenyl)-8-[4-(5-methyl-2-phenyl-4-oxazolylmethoxy)benzyloxyimino]octanoate (828 mg, yield 75%) as a colorless oil from an ethyl acetate-hexane (1:6, v/v)-eluted fraction.

Aufarbeitung

  1. temperaturewas heated
  2. temperatureto reflux for 18 hours
  3. extractionextracted with ethyl acetate
  4. washThe ethyl acetate layer was washed with an aqueous saturated solution of sodium chloride
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-6b8a2bea5f0843b1bdf42454c2a29a36
Quelldatensatz
uspto-grants-2002_12
Patentnummer
US06495581B1

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