1-[2-Hydroxy-4-(3-nitro-benzyloxy)-3-propyl-phenyl]-ethanone → 1-{4-[(3-Aminophenyl)methoxy]-2-hydroxy-3-propylphenyl}ethan-1-one

HRID 2267029Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2267029
[OH:1][C:2]1[C:7]([CH2:8][CH2:9][CH3:10])=[C:6]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([N+:19]([O-])=O)[CH:14]=2)[CH:5]=[CH:4][C:3]=1[C:22](=[O:24])[CH3:23]>C(O)(=O)C.ClCCl.[Zn]>[NH2:19][C:15]1[CH:14]=[C:13]([CH:18]=[CH:17][CH:16]=1)[CH2:12][O:11][C:6]1[CH:5]=[CH:4][C:3]([C:22](=[O:24])[CH3:23])=[C:2]([OH:1])[C:7]=1[CH2:8][CH2:9][CH3:10]

Komponenten

5

Edukt 1

HCID 684320061-[2-Hydroxy-4-(3-nitro-benzyloxy)-3-propyl-phenyl]-ethanone

Produkt 1

HCID 145235601-{4-[(3-Aminophenyl)methoxy]-2-hydroxy-3-propylphenyl}ethan-1-oneAusbeute 536,6 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 23994ZincKatalysatorHCID 176Acetic AcidLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Add zinc (21.6 g, 331 mmol) slowly to a solution of 1-[2-hydroxy-4-(3-nitro-benzyloxy)-3-propyl-phenyl]-ethanone (10.9 g, 6.07 mmol) in glacial acetic acid (120 mL). Stir the mixture for 3 hours. Dilute with dichloromethane (600 mL). Filter the reaction mixture through celite. Wash the celite pad several times with dichloromethane. Concentrate the combined filtrates. Partition the residue between ethyl acetate and saturated sodium bicarbonate. Wash the organic layer with brine, dry and concentrate to afford the title compound as a yellow solid (9.75 g, 98%): 1H NMR (CDCl3) δ 0.96 (t, 3H), 1.58 (sextet, 2H), 2.54 (s, 3H), 2.71 (t, 2H), 5.07 (s, 2H), 6.46 (d, 1H), 6.62 (d, 1H), 6.71 (s, 1H), 6.78 (d, 1H), 7.16 (t, 1H), 7.54 (d, 1H), 12.75 (s, 1H).

Aufarbeitung

  1. filtrationFilter the reaction mixture through celite
  2. washWash the celite pad several times with dichloromethane
  3. concentrationConcentrate the combined filtrates
  4. customPartition the residue between ethyl acetate and saturated sodium bicarbonate
  5. washWash the organic layer with brine
  6. customdry
  7. concentrationconcentrate

Quellen und Nachweise

ORD-Eintrag
ord-2cba0cf60e604add8a0f1f9d8d2dd463
Quelldatensatz
uspto-grants-2010_12
Patentnummer
US07858646B2

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