4-bromo-6-methoxy-2,2-dimethyl-3,4-dihydronaphthalen-1(2H)-one → 4-azido-6-methoxy-2,2-dimethyl-3,4-dihydronaphthalen-1(2H)-one

HRID 253152Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 253152
Br[CH:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([O:12][CH3:13])[CH:10]=2)[C:5](=[O:14])[C:4]([CH3:16])([CH3:15])[CH2:3]1.[N:17]([Na])=[N+:18]=[N-:19]>CN(C=O)C>[N:17]([CH:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([O:12][CH3:13])[CH:10]=2)[C:5](=[O:14])[C:4]([CH3:16])([CH3:15])[CH2:3]1)=[N+:18]=[N-:19]

Komponenten

4

Edukt 2

HCID 668447194-bromo-6-methoxy-2,2-dimethyl-3,4-dihydronaphthalen-1(2H)-oneHCID 178514644HCID 178514644, Verbindung

Produkt 1

HCID 866140234-azido-6-methoxy-2,2-dimethyl-3,4-dihydronaphthalen-1(2H)-oneAusbeute 90 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

4-Bromo-6-methoxy-2,2-dimethyl-3,4-dihydronaphthalen-1(2H)-one (3.9 g, 14 mmol) was added to DMF (10 mL) followed by azidosodium (3.6 g, 55 mmol). The mixture was heated to 60° C. overnight. The reaction was cooled to RT and quenched with water (25 mL). The aqueous layer was extracted with Et2O (3×100 mL). The combined organic layers were washed with brine, dried over MgSO4 and filtered. The solvent was evaporated and the residue was purified by column chromatography (0-50% EtOAc/Hexane to provide the title compound as a white solid (3.05 g, 90% yield). MS m/z: 268.2 (M+Na).

Aufarbeitung

  1. temperatureThe reaction was cooled to RT
  2. customquenched with water (25 mL)
  3. extractionThe aqueous layer was extracted with Et2O (3×100 mL)
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customThe solvent was evaporated
  8. customthe residue was purified by column chromatography (0-50% EtOAc/Hexane

Quellen und Nachweise

ORD-Eintrag
ord-38afeb4e81324e23b8865bdfcdab89e6
Quelldatensatz
uspto-grants-2011_01
Patentnummer
US07872009B2

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