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Potassium Carbonate → Tert-butyl 3-methoxy-4-((6-methoxypyridin-3-yl)methoxy)benzylcarbamate

HRID 2178301
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2178301
[OH:1][C:2]1[CH:16]=[CH:15][C:5]([CH2:6][NH:7][C:8](=[O:14])[O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[CH:4][C:3]=1[O:17][CH3:18].C(=O)([O-])[O-].[K+].[K+].Cl.Cl[CH2:27][C:28]1[CH:29]=[CH:30][C:31]([O:34][CH3:35])=[N:32][CH:33]=1>C(#N)C.O>[CH3:18][O:17][C:3]1[CH:4]=[C:5]([CH:15]=[CH:16][C:2]=1[O:1][CH2:27][C:28]1[CH:33]=[N:32][C:31]([O:34][CH3:35])=[CH:30][CH:29]=1)[CH2:6][NH:7][C:8](=[O:14])[O:9][C:10]([CH3:13])([CH3:12])[CH3:11]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 3

HCID 11430Potassium CarbonateHCID 15713917tert-butyl 4-hydroxy-3-MethoxybenzylcarbaMateHCID 534389575-(Chloromethyl)-2-methoxypyridine hydrochloride

Produkt 1

HCID 118114124Tert-butyl 3-methoxy-4-((6-methoxypyridin-3-yl)methoxy)benzylcarbamateAusbeute 96,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962
Water
Lösungsmittel
HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

To a stirred solution of tert-butyl 4-hydroxy-3-methoxybenzylcarbamate (22.44 g, 88.59 mmol) in acetonitrile (250 mL) was added potassium carbonate (30.61 g, 221.5 mmol) and 5-(chloromethyl)-2-methoxypyridine hydrochloride (18.33 g, 94.46 mmol). The resulting mixture was heated to reflux and stirred. After 23 h, the light green suspension was allowed to cool to room temperature and was diluted with water (600 mL), resulting in the formation of a precipitate. The solids were isolated by filtration and washed with water. The moist solids were dissolved in dichloromethane (300 mL), and a small amount of water separated and was removed. The organic phase was dried over magnesium sulfate, filtered, and concentrated to provide 31.92 g (96%) of tert-butyl 3-methoxy-4-((6-methoxypyridin-3-yl)methoxy)benzylcarbamate as an off-white solid.

Aufarbeitung

  1. temperatureThe resulting mixture was heated
  2. temperatureto reflux
  3. customresulting in the formation of a precipitate
  4. customThe solids were isolated by filtration
  5. washwashed with water
  6. dissolutionThe moist solids were dissolved in dichloromethane (300 mL)
  7. customa small amount of water separated
  8. customwas removed
  9. dry with materialThe organic phase was dried over magnesium sulfate
  10. filtrationfiltered
  11. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-3acfe7501ca9470598f470eb681724c2
Quelldatensatz
uspto-grants-2015_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09067914B1

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