1-(3-Hydroxy-4-methoxyphenyl)ethanone → 5-[(E)-N-[(3-fluorophenyl)methoxy]-C-methylcarbonimidoyl]-2-methoxyphenol

HRID 41934

Reaktionsgleichung

Reaktionsgleichung von HRID 41934
[OH:1][C:2]1[CH:3]=[C:4]([C:10](=O)[CH3:11])[CH:5]=[CH:6][C:7]=1[O:8][CH3:9].Cl.[F:14][C:15]1[CH:16]=[C:17]([CH:21]=[CH:22][CH:23]=1)[CH2:18][O:19][NH2:20]>>[F:14][C:15]1[CH:16]=[C:17]([CH:21]=[CH:22][CH:23]=1)[CH2:18][O:19]/[N:20]=[C:10](/[C:4]1[CH:5]=[CH:6][C:7]([O:8][CH3:9])=[C:2]([OH:1])[CH:3]=1)\[CH3:11]

Komponenten

3

Edukt 2

HCID 956931-(3-Hydroxy-4-methoxyphenyl)ethanoneHCID 23206139o-(3-Fluorobenzyl)hydroxylamine hydrochloride

Produkt 1

HCID 885675655-[(E)-N-[(3-fluorophenyl)methoxy]-C-methylcarbonimidoyl]-2-methoxyphenolAusbeute 82 %

Versuchsvorschrift

Acetophenone 12 (50 mg, 0.301 mmol) was condensed with O-(3-fluorobenzyl)hydroxylamine hydrochloride (26) (59 mg, 0.332 mmol) according to the general procedure II-B defined above. After being heated at reflux for 48 h the reaction mixture was cooled and the solvent removed under reduced pressure. The ensuing residue was dissolved in CH2Cl2 (15 mL), washed with H2O (2×10 mL) then dried (MgSO4), filtered and concentrated under reduced pressure. The oil thus obtained was subjected to flash chromatography (1:19 v/v ethyl acetate/hexane elution) to afford the title compound CP30262 (71 mg, 82%) as a pale-pink oil, Rf 0.6 in 1:1 v/v ethyl acetate/hexane.

Aufarbeitung

  1. temperatureAfter being heated
  2. temperatureat reflux for 48 h the reaction mixture
  3. temperaturewas cooled
  4. customthe solvent removed under reduced pressure
  5. dissolutionThe ensuing residue was dissolved in CH2Cl2 (15 mL)
  6. washwashed with H2O (2×10 mL)
  7. dry with materialthen dried (MgSO4)
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure
  10. customThe oil thus obtained
  11. washwas subjected to flash chromatography (1:19 v/v ethyl acetate/hexane elution)

Quellen und Nachweise

ORD-Eintrag
ord-a9c2afbe137c477db6b96e4a436d9048
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08536157B2

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