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Sodium Hydroxide → HCID 11141777, Verbindung

HRID 377566
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 377566
[OH-].[Na+].[CH3:3][S:4][CH2:5][C:6]1[O:11][CH2:10][N:9]([C:12]([CH3:19])([CH3:18])[C:13]([O:15]CC)=[O:14])[C:8](=[O:20])[C:7]=1[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>C(O)C.O1CCOCC1.O>[CH3:3][S:4][CH2:5][C:6]1[O:11][CH2:10][N:9]([C:12]([CH3:19])([CH3:18])[C:13]([OH:15])=[O:14])[C:8](=[O:20])[C:7]=1[C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 2

HCID 14798Sodium HydroxideHCID 19354572HCID 19354572, Verbindung

Produkt 1

HCID 11141777HCID 11141777, VerbindungAusbeute 38,7 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 702EthanolLösungsmittelHCID 962WaterLösungsmittel2×
HCID 31275
1,4-Dioxane
Lösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

A solution of sodium hydroxide (16.43 g) in 10 water was added to a stirred solution of ethyl 2-(2,3-dihydro-6-methylthiomethyl-4-oxo-5-phenyl-4H-1,3-oxazin-3-yl)-2-methylpropanoate (68 g) in a mixture of ethanol and 1,4-dioxan. The solution was heated at 60° C. for 6 hours, allowed to cool and the solvent was removed under reduced pressure to give an orange oil which was dissolved in water. The aqueous solution was washed with dichloromethane, acidified to pH 1 with concentrated hydrochloric acid, extracted with dichloromethane, the extract dried (magnesium sulphate) and evaporated under reduced pressure. The residue was purified by chromatography on silica gel, eluting with dichloromethane/ethyl acetate to give 2-(2,3-dihydro-6-methylthiomethyl-4-oxo-5-phenyl-4H-1,3-oxazin-3-yl)-2-methylpropanoic acid (24.2 g) as a yellow solid, m.p. 136-137° C.

Aufarbeitung

  1. temperatureto cool
  2. customthe solvent was removed under reduced pressure
  3. customto give an orange oil which
  4. washThe aqueous solution was washed with dichloromethane
  5. extractionextracted with dichloromethane
  6. dry with materialthe extract dried (magnesium sulphate)
  7. customevaporated under reduced pressure
  8. customThe residue was purified by chromatography on silica gel
  9. washeluting with dichloromethane/ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-58038c6d686241d8b1c4fd33627180f6
Quelldatensatz
uspto-grants-2000_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06028032

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