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Triethylamine → N-hydroxy-2,2-dimethylspiro[1,3-dioxane-5,2'-inden]-1'(3'H)-imine

HRID 64451
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 64451
[CH3:1][C:2]1([CH3:17])[O:16][CH2:15][C:5]2([CH2:13][C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[C:6]2=O)[CH2:4][O:3]1.Cl.[NH2:19][OH:20].C([O-])(=O)C.[Na+].C(N(CC)CC)C>C(O)C.C(OCC)(=O)C.O>[OH:20][N:19]=[C:6]1[C:7]2[C:12](=[CH:11][CH:10]=[CH:9][CH:8]=2)[CH2:13][C:5]21[CH2:15][O:16][C:2]([CH3:17])([CH3:1])[O:3][CH2:4]2
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

8

Edukt 4

HCID 8471TriethylamineHCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 71108842HCID 71108842, Verbindung

Produkt 1

HCID 86713466N-hydroxy-2,2-dimethylspiro[1,3-dioxane-5,2'-inden]-1'(3'H)-imineAusbeute 93,9 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 702
Ethanol
Lösungsmittel
HCID 962WaterLösungsmittel
HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A suspension of 1 g of 2,2-dimethylspiro[1,3-dioxane-5,2′-inden]-1′(3′H)-one, 329 mg of hydroxylamine hydrochloride, and 388 mg of sodium acetate in 5 ml of ethanol was stirred for 12 hours. Then, 1.2 ml of triethylamine was added thereto, followed by stirring at room temperature for 3 days and further stirring at 50° C. for 1 hour. To the reaction mixture were added water and ethyl acetate to carry out a layer separation operation. The organic layer was washed with water and saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography to obtain 1.0 g of N-hydroxy-2,2-dimethylspiro[1,3-dioxane-5,2′-inden]-1′(3′H)-imine.

Aufarbeitung

  1. stirringby stirring at room temperature for 3 days
  2. stirringfurther stirring at 50° C. for 1 hour
  3. customa layer separation operation
  4. washThe organic layer was washed with water and saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customthe solvent was evaporated under reduced pressure
  7. customThe obtained residue was purified by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-bd9a5799797542bea9c5897d9a74b661
Quelldatensatz
uspto-grants-2016_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09447090B2

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