4-Nitrophenol → 4-(3,3-Diethyl-4-oxo-2-azetidinyl)oxy-nitrobenzene

HRID 484193Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 484193
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1)([O-:3])=[O:2].C([O:14][CH:15]1[C:18]([CH2:21][CH3:22])([CH2:19][CH3:20])[C:17](=O)[NH:16]1)(=O)C.C(OCC)(=O)C>[OH-].[Na+].CC(C)=O>[CH2:19]([C:18]1([CH2:21][CH3:22])[C:15](=[O:14])[NH:16][CH:17]1[O:10][C:7]1[CH:8]=[CH:9][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=1)[CH3:20]

Komponenten

6

Edukt 3

HCID 9804-NitrophenolHCID 8857Ethyl AcetateHCID 102618172-Azetidinone, 4-(acetyloxy)-3,3-diethyl-

Produkt 1

HCID 197510524-(3,3-Diethyl-4-oxo-2-azetidinyl)oxy-nitrobenzeneAusbeute 80 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 180AcetoneLösungsmittelHCID 14798Sodium HydroxideLösungsmittel

Versuchsvorschrift

A solution of 4-nitrophenol (2.37 gm, 17.0 mmol) in 2.5N sodium hydroxide (6.82 mL) was added to a solution of 2-acetoxy-3,3-diethyl-4-oxoazetidine (1.05 gm, 5.7 mmol) in acetone (5 mL). After stirring at room temperature for 2.5 hours, ethyl acetate (100 mL) was added and the solution successively washed with water (3×20 mL) and saturated salt solution (20 mL). The solution was dried over anhydrous sodium sulfate and the solvent removed by rotoevaporated. The product was purified by flash column chromatography on silica gel eluted with 25% ethyl acetate in hexanes and isolated as a beige solid (1.20 gm, 80% yield): 1H-NMR δ (CDCl3) 0.94 (6H, t, J=7 Hz), 1.62-1.92 (4H, m), 5.38 (1H, s), 6.90 (2H, d, J=9 Hz), 7.66 (1H, s), 8.10 (2H, d, J= 9 Hz).

Aufarbeitung

  1. washthe solution successively washed with water (3×20 mL) and saturated salt solution (20 mL)
  2. dry with materialThe solution was dried over anhydrous sodium sulfate
  3. customthe solvent removed by rotoevaporated
  4. customThe product was purified by flash column chromatography on silica gel
  5. washeluted with 25% ethyl acetate in hexanes

Quellen und Nachweise

ORD-Eintrag
ord-47fcd469570a4fe8a37201780bbace37
Quelldatensatz
uspto-grants-1993_07
Patentnummer
US05229510

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