1,4-Dioxane → HCID 15027354, Verbindung

HRID 1195863Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1195863
[OH:1][NH:2][CH2:3][C:4]1[CH:16]=[CH:15][C:14]2[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[CH2:7][C:6]=2[CH:5]=1.CC([O-])=[O:19].[Na+].[O:22]1[CH2:27][CH2:26][O:25][CH2:24][CH2:23]1>O>[CH:5]1[C:6]2[CH2:7][C:8]3[C:13](=[CH:12][CH:11]=[CH:10][CH:9]=3)[C:14]=2[CH:15]=[CH:16][C:4]=1[CH2:3][N:2]([C:24](=[O:25])[C:23]([O:22][CH2:27][CH3:26])=[O:19])[OH:1]

Komponenten

5

Edukt 3

HCID 312751,4-DioxaneHCID 517045Sodium AcetateHCID 15027353HCID 15027353, Verbindung

Produkt 1

HCID 15027354HCID 15027354, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
-5 °C

Versuchsvorschrift

The crude hydroxylamine (4.2 g, 0.02 mol) from Example 1 is dissolved in dioxane (80 ml) and water (50 ml). The turbid solution is cooled to -5° C. and then treated with NaOAc (3.3 g, 0.04 mol) followed by ethyl oxalylchloride (3.0 g, 0.022 mol). The mixture is stirred at 24° C. for 3.0 hours, poured onto ice-1N HCl (40 mL) and extracted with CH2Cl2. The extract is washed with brine, water and dried over Na2SO4. The solvent is distilled off to give (9H-fluoren-2-ylmethyl)hydroxyamino-oxo-acetic acid, ethyl ester which is fractionally recrystallized from isopropyl ether and CH2Cl2 and then from isopropyl ether. Yield 1.6 g (26%); mp 130°-131° C.

Aufarbeitung

  1. additionpoured onto ice-1N HCl (40 mL)
  2. extractionextracted with CH2Cl2
  3. washThe extract is washed with brine, water
  4. dry with materialdried over Na2SO4
  5. distillationThe solvent is distilled off

Quellen und Nachweise

ORD-Eintrag
ord-69ecdf80ac864a478165e7bc6f918bd3
Quelldatensatz
uspto-grants-1992_05
Patentnummer
US05112846

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