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Sodium Hydroxide → 2-Chloro-6-morpholinopyran-4-one

HRID 33780
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 33780
[Cl:1][C:2](Cl)=[CH:3][C:4](=[O:14])[CH2:5][C:6]([N:8]1[CH2:13][CH2:12][O:11][CH2:10][CH2:9]1)=[O:7].Cl(O)(=O)(=O)=O.[OH-].[Na+]>O1CCOCC1>[Cl:1][C:2]1[O:7][C:6]([N:8]2[CH2:13][CH2:12][O:11][CH2:10][CH2:9]2)=[CH:5][C:4](=[O:14])[CH:3]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 14798Sodium HydroxideHCID 24247Perchloric AcidHCID 66052615,5-Dichloro-1-morpholinopent-4-ene-1,3-dione

Produkt 1

HCID 66052622-Chloro-6-morpholinopyran-4-oneAusbeute 75,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

To a suspension of 2 (11.3 g, 44.9 mmol) in dioxane was added perchloric acid (11.4 ml, 0.14 mol) and the reaction was heated at 90° C. under N2 for 1 hour. The reaction was cooled, neutralised with 2M NaOH (75 ml) and filtered. The aqueous layer was extracted with DCM (4×30 ml) and the organic layers were combined and dried over MgSO4. The organic layer was further treated with charcoal and filtered through celite. The dark yellow filtrate was evaporated in vacuo, and the resulting solid was triturated with hexane (50 ml) and dried to give 3 (7.3 g, 75%) as a light yellow powder. m/z (LC-MS, ESP): 216 (M++1). 1H-NMR (300 MHz, DMSO-d6): 3.3 (t, 4H), 3.65 (t, 4H), 5.4 (d, 1H), 6.25 (d, 1H).

Aufarbeitung

  1. temperatureThe reaction was cooled
  2. filtrationfiltered
  3. extractionThe aqueous layer was extracted with DCM (4×30 ml)
  4. dry with materialdried over MgSO4
  5. additionThe organic layer was further treated with charcoal
  6. filtrationfiltered through celite
  7. customThe dark yellow filtrate was evaporated in vacuo
  8. customthe resulting solid was triturated with hexane (50 ml)
  9. customdried

Quellen und Nachweise

ORD-Eintrag
ord-39173e7f8abd44aa9174da35c16bc802
Quelldatensatz
uspto-grants-2008_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07429660B2

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