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

HRID 41938

Reaktionsgleichung

Reaktionsgleichung von HRID 41938
[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:23]=[CH:22][CH:21]=[CH:20][C:16]=1[CH2:17][O:18][NH2:19]>C(OCC)(=O)C.CCCCCC>[F:14][C:15]1[CH:23]=[CH:22][CH:21]=[CH:20][C:16]=1[CH2:17][O:18]/[N:19]=[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

4

Edukt 2

HCID 956931-(3-Hydroxy-4-methoxyphenyl)ethanoneHCID 21192890O-(2-Fluorobenzyl)hydroxylamine hydrochloride

Produkt 1

HCID 251004085-[(E)-N-[(2-fluorophenyl)methoxy]-C-methylcarbonimidoyl]-2-methoxyphenolAusbeute 91 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 21226206Ethyl acetate hexaneLösungsmittel2×

Versuchsvorschrift

Acetophenone 12 (50 mg, 0.301 mmol) was condensed with O-(2-fluorobenzyl)hydroxylamine hydrochloride (32) (58 mg, 0.327 mmol) according to the general procedure II-B defined above. After being heated for 36 h the reaction mixture was cooled and the solvent removed under reduced pressure. The ensuing residue was dissolved in CH2Cl2 (15 mL) and the resulting solution 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) to afford the title compound CP30280 (79 mg, 91%) as a pale-yellow oil, Rf 0.5 in 1:1 v/v ethyl acetate/hexane.

Aufarbeitung

  1. temperatureAfter being heated for 36 h the reaction mixture
  2. temperaturewas cooled
  3. customthe solvent removed under reduced pressure
  4. dissolutionThe ensuing residue was dissolved in CH2Cl2 (15 mL)
  5. washthe resulting solution washed with H2O (2×10 mL)
  6. dry with materialthen dried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThe oil thus obtained

Quellen und Nachweise

ORD-Eintrag
ord-a1cb47cc8f73450e8f575565cb87c1e6
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08536157B2

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