4-Benzyloxy-N-methoxy-N-methylphenylacetamide → 1-(4-Benzyloxy-phenyl)-pentan-2-one

HRID 1971892Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1971892
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][C:16](N(OC)C)=[O:17])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:22]([Mg]Br)[CH2:23][CH3:24]>C1COCC1>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([CH2:15][C:16](=[O:17])[CH2:22][CH2:23][CH3:24])=[CH:13][CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

4

Edukt 2

HCID 112546484-Benzyloxy-N-methoxy-N-methylphenylacetamideHCID 178455851HCID 178455851, Verbindung

Produkt 1

HCID 673733611-(4-Benzyloxy-phenyl)-pentan-2-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a stirred solution of 2-(4-benzyloxy-phenyl)-N-methoxy-N-methyl-acetamide (10.51 mmol, 3.0 g) in anhydrous THF at 0° C. was added n-propyl magnesium bromide (2.0 M solution in THF, 20 mL) drop-wise over 30 min. After completion of addition, the reaction mixture was warmed to room temperature and stirred for 30 min. The reaction mixture was cooled to 0° C. and quenched by adding saturated aqueous NH4Cl drop-wise followed by addition of ethyl acetate. The organic layer was separated, dried, filtered, and concentrated under reduced pressure. The residue was purified by flash column chromatography by eluting with 5% ethyl acetate in hexanes to provide 1-(4-benzyloxy-phenyl)-pentan-2-one.

Aufarbeitung

  1. additionAfter completion of addition
  2. temperatureThe reaction mixture was cooled to 0° C.
  3. customquenched
  4. additionby adding saturated aqueous NH4Cl
  5. additiondrop-wise followed by addition of ethyl acetate
  6. customThe organic layer was separated
  7. customdried
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure
  10. customThe residue was purified by flash column chromatography
  11. washby eluting with 5% ethyl acetate in hexanes

Quellen und Nachweise

ORD-Eintrag
ord-3f9ec5f44c214629a6d770d3aa0ea268
Quelldatensatz
uspto-grants-2013_04
Patentnummer
US08431575B2

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