Acetic Anhydride → N-{2-[(2S)-Oxiran-2-ylmethoxy]phenyl}acetamide
Reaktionsgleichung
[N+:1]([C:4]1[CH:14]=[CH:13][CH:12]=[CH:11][C:5]=1[O:6][CH2:7][C@@H:8]1[CH2:10][O:9]1)([O-])=O.[H][H].[C:17](OC(=O)C)(=[O:19])[CH3:18].C(N(C(C)C)C(C)C)C>C(OCC)(=O)C.[Pt]>[O:9]1[CH2:10][C@H:8]1[CH2:7][O:6][C:5]1[CH:11]=[CH:12][CH:13]=[CH:14][C:4]=1[NH:1][C:17](=[O:19])[CH3:18]Komponenten
Edukt 4
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 2
Versuchsvorschrift
(2S)-2-[(2-nitrophenoxy)methyl]oxirane (1.17 g, 6 mmol) was dissolved in ethyl acetate (50 ml). Platinum on charcoal (0.50 g) was added, and the mixture was stirred in the atmosphere of hydrogen for 3 h at room temperature and atmospheric pressure. The catalyst was filtered and washed on the filter with ethyl acetate (10 ml). Acetic anhydride (1.23 g, 1.13 ml, 12 mmol) and ethyldi(i-propyl)amine (1.55 g, 2.05 ml, 12 mmol) were added to the solution. The reaction mixture was stirred at room temperature for 3 h, then washed with 1M NaOH (2×50 ml) and brine (2×50 ml), and dried with Na2SO4. Evaporation of the solvent and flash chromatography on silica gel with n-heptane/ethyl acetate (from 25 to 75%) afforded the title compound (0.74 g, 3.57 mmol, 60%) as colourless crystals.
Aufarbeitung
- filtrationThe catalyst was filtered
- washwashed on the
- filtrationfilter with ethyl acetate (10 ml)
- washwashed with 1M NaOH (2×50 ml) and brine (2×50 ml)
- dry with materialdried with Na2SO4
- customEvaporation of the solvent and flash chromatography on silica gel with n-heptane/ethyl acetate (from 25 to 75%)
Quellen und Nachweise
- ORD-Eintrag
- ord-a09d5949b2b64b7c9f4a6c9d6270e4f7
- Quelldatensatz
- uspto-grants-2009_05
- Patentnummer
- US07528156B2
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