Dimethylformamide → N-[4-Methyl-2-(2-oxiranylmethoxy)phenyl]acetamide

HRID 490322Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 490322
OC[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[NH:9][C:10](=[O:12])[CH3:11].Br[CH2:14][CH:15]1C[O:16]1.[C:18](=[O:21])([O-])[O-].[K+].[K+].[CH3:24]N(C=O)C>C(OCC)(=O)C>[CH3:24][C:7]1[CH:6]=[CH:5][C:4]([NH:9][C:10](=[O:12])[CH3:11])=[C:3]([O:16][CH2:15][CH:14]2[CH2:18][O:21]2)[CH:8]=1

Komponenten

6

Edukt 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 18430EpibromohydrinHCID 3392922-Acetamidobenzyl alcohol

Produkt 1

HCID 22386970N-[4-Methyl-2-(2-oxiranylmethoxy)phenyl]acetamideAusbeute 43 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
55 °C

Versuchsvorschrift

A mixture of N-(2-hydroxymethylphenyl)acetamide (10 g, 60 mmol), 2-(bromomethyl)oxirane (9.86 g, 72 mmol, 6.0 ml) and potassium carbonate (16.8 g, 120 mmol) in DMF (100 ml) was heated at 55° C. for 2 h. Then the reaction mixture was diluted with ethyl acetate and washed with aq. HCl (1.5%), aq sat. NaHCO3, and brine. Evaporation of the solvent and flash chromatography on silica gel with n-heptane/ethyl acetate (ethyl acetate from 35 to 70%) afforded the title compound (5.65 g, 25 mmol, 43%).

Aufarbeitung

  1. washwashed with aq. HCl (1.5%), aq sat. NaHCO3, and brine
  2. customEvaporation of the solvent and flash chromatography on silica gel with n-heptane/ethyl acetate (ethyl acetate from 35 to 70%)

Quellen und Nachweise

ORD-Eintrag
ord-80c973c659fa4aa28443f829cf92990e
Quelldatensatz
uspto-grants-2009_05
Patentnummer
US07528156B2

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