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

HRID 1971866Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1971866
[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]Cl)[CH2:23][CH2:24][CH3:25]>C1COCC1>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([CH2:15][C:16](=[O:17])[CH2:22][CH2:23][CH2:24][CH3:25])=[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 178418265HCID 178418265, Verbindung

Produkt 1

HCID 673734141-(4-Benzyloxy-phenyl)-hexan-2-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a stirred solution of 2-(4-benzyloxy-phenyl)-N-methoxy-N-methyl-acetamide (42.1 mmol, 12.0 g) in anhydrous THF at −10° C. was added n-butyl magnesium chloride (2.0 M solution in THF, 92.6 mmol, 46.3 mL) drop-wise. 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 with 1.0 N HCl by adding drop-wise. The reaction mixture was poured into water, extracted with ethyl acetate, and the combined extract was washed with water followed by brine. The organic layer was dried (Na2SO4), filtered and concentrated under reduced pressure. The resultant residue was purified by column chromatography using 10% ethyl acetate in hexanes to provide 1-(4-benzyloxy-phenyl)-hexan-2-one.

Aufarbeitung

  1. additionAfter completion of addition
  2. temperatureThe reaction mixture was cooled to 0° C.
  3. customquenched with 1.0 N HCl
  4. additionby adding drop-wise
  5. additionThe reaction mixture was poured into water
  6. extractionextracted with ethyl acetate
  7. extractionthe combined extract
  8. washwas washed with water
  9. dry with materialThe organic layer was dried (Na2SO4)
  10. filtrationfiltered
  11. concentrationconcentrated under reduced pressure
  12. customThe resultant residue was purified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-ea99d529d5ce4b3b8fdf57881a5382ed
Quelldatensatz
uspto-grants-2013_04
Patentnummer
US08431575B2

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