Hydrochloric Acid → 1,5-Bis-(4-nitro-phenyl)-pentan-3-one

HRID 1003831Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1003831
C(OC(=O)[CH:5]([CH2:19][C:20]1[CH:25]=[CH:24][C:23]([N+:26]([O-:28])=[O:27])=[CH:22][CH:21]=1)[C:6](=[O:18])[CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([N+:15]([O-:17])=[O:16])=[CH:11][CH:10]=1)C.Cl.C1COCC1>O>[N+:15]([C:12]1[CH:13]=[CH:14][C:9]([CH2:8][CH2:7][C:6](=[O:18])[CH2:5][CH2:19][C:20]2[CH:25]=[CH:24][C:23]([N+:26]([O-:28])=[O:27])=[CH:22][CH:21]=2)=[CH:10][CH:11]=1)([O-:17])=[O:16]

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 543227172-(4-Nitro-benzyl)-5-(4-nitro-phenyl)-3-oxo-pentanoic acid ethyl ester

Produkt 1

HCID 187986641,5-Bis-(4-nitro-phenyl)-pentan-3-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

A mixture of 2-(4-nitro-benzyl)-5-(4-nitro-phenyl)-3-oxo-pentanoic acid ethyl ester obtained in Example GG (18.2 g, 45.4 mmol), 6N HCl (250 mL), and THF (50 mL) was refluxed for 18 hours and cooled to room temperature. H2O was added, and the solution was extracted with EtOAc. The extracts were combined, washed with brine, dried (MgSO4), and concentrated. The residue was triturated with Et2O and filtered to give the title compound. 1H NMR (CDCl3) δ2.73 (t, 4 H), 2.96 (t, 4 H), 7.29 (d, 4 H), 8.09 (m, 4 H).

Aufarbeitung

  1. temperaturewas refluxed for 18 hours
  2. extractionthe solution was extracted with EtOAc
  3. washwashed with brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated
  6. customThe residue was triturated with Et2O
  7. filtrationfiltered

Quellen und Nachweise

ORD-Eintrag
ord-ee320aabe0b84c3a9994840c274a378a
Quelldatensatz
uspto-grants-2000_04
Patentnummer
US06046355

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