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Acetic Anhydride → HCID 59792534, Verbindung

HRID 1645562
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1645562
[CH2:1]1[C:4]2([O:9][CH2:8][CH:7]([CH2:10][O:11][C:12]3[C:17]([CH3:18])=[CH:16][N+:15]([O-])=[C:14]([CH3:20])[C:13]=3[CH3:21])[CH2:6][O:5]2)[CH2:3][CH2:2]1.C(OC(=O)C)(=[O:24])C.[OH-].[Na+]>CO>[CH2:1]1[C:4]2([O:9][CH2:8][CH:7]([CH2:10][O:11][C:12]3[C:17]([CH3:18])=[CH:16][N:15]=[C:14]([CH2:20][OH:24])[C:13]=3[CH3:21])[CH2:6][O:5]2)[CH2:3][CH2:2]1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 7918Acetic AnhydrideHCID 14798Sodium HydroxideHCID 59792344Pyridine, 4-(5,9-dioxaspiro[3.5]non-7-ylmethoxy)-2,3,5-trimethyl-, 1-oxide

Produkt 1

HCID 59792534HCID 59792534, VerbindungAusbeute 85,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Reaktionsbedingungen

Temperatur
85 °C

Versuchsvorschrift

The 4-(5,9-dioxaspiro[3.5]non-7-ylmethoxy)-2,3,5-trimethylpyridine 1-oxide (1.97 g, 6.72 mmol) obtained in the step (13b) was mixed with acetic anhydride (20 ml, 212 mmol). The mixture was stirred at 85° C. for 1.5 hours. After cooled to room temperature, the reaction mixture was concentrated. To the residue, methanol (20 ml) and a 5N aqueous sodium hydroxide solution (20 ml, 100 mmol) were added and the mixture was stirred at room temperature for 45 minutes. The reaction mixture was concentrated and the residue was partitioned between water and ethyl acetate. The organic layer was washed with a 2N aqueous sodium hydroxide solution, dried over anhydrous magnesium sulfate, filtered and concentrated to obtain the title compound (1.69 g, yield: 85.7%) as a brown oil.

Aufarbeitung

  1. temperatureAfter cooled to room temperature
  2. concentrationthe reaction mixture was concentrated
  3. stirringthe mixture was stirred at room temperature for 45 minutes
  4. concentrationThe reaction mixture was concentrated
  5. customthe residue was partitioned between water and ethyl acetate
  6. washThe organic layer was washed with a 2N aqueous sodium hydroxide solution
  7. dry with materialdried over anhydrous magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-28363176e5e14583858fde116548cad3
Quelldatensatz
uspto-grants-2012_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08124780B2

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