Potassium Carbonate → Ethyl (2S)-2-ethoxy-3-{4-[4-(4-nitrophenyl)butoxy]phenyl}propanoate

HRID 1375719Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1375719
[CH2:1]([O:3][C:4](=[O:17])[C@@H:5]([O:14][CH2:15][CH3:16])[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([OH:13])=[CH:9][CH:8]=1)[CH3:2].CS(O[CH2:23][CH2:24][CH2:25][CH2:26][C:27]1[CH:32]=[CH:31][C:30]([N+:33]([O-:35])=[O:34])=[CH:29][CH:28]=1)(=O)=O.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[CH2:15]([O:14][C@@H:5]([CH2:6][C:7]1[CH:8]=[CH:9][C:10]([O:13][CH2:23][CH2:24][CH2:25][CH2:26][C:27]2[CH:32]=[CH:31][C:30]([N+:33]([O-:35])=[O:34])=[CH:29][CH:28]=2)=[CH:11][CH:12]=1)[C:4]([O:3][CH2:1][CH3:2])=[O:17])[CH3:16]

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 9816147Ethyl (2S)-2-ethoxy-3-(4-hydroxyphenyl)propanoateHCID 147295324-(4-Nitrophenyl)butyl methanesulfonate

Produkt 1

HCID 86613338Ethyl (2S)-2-ethoxy-3-{4-[4-(4-nitrophenyl)butoxy]phenyl}propanoateAusbeute 93 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

(S)-2-Ethoxy-3-(4-hydroxyphenyl)propanoic acid ethyl ester (1.0 g, 4.197 mmol) and 4-(4-nitrophenyl)butyl methanesulfonate (1.204 g, 4.406 mmol) were mixed in acetonitrile (20 ml). Potassium carbonate (anhydrous, 870 mg, 6.295 mmol) was added. The mixture was heated to reflux overnight. It was then evaporated in vacuum. Water and ethyl acetate were added into the residue. The two phases were separated. The organic phase was washed with water and brine and dried with magnesium sulfate. The solvent was removed by evaporation in vacuum. Column chromatography of the residue on silica gel using ethyl acetate/heptane (25:75) as eluant gave the desired product (1.62 g), yield 93%.

Aufarbeitung

  1. temperatureThe mixture was heated
  2. temperatureto reflux overnight
  3. customIt was then evaporated in vacuum
  4. additionWater and ethyl acetate were added into the residue
  5. customThe two phases were separated
  6. washThe organic phase was washed with water and brine
  7. dry with materialdried with magnesium sulfate
  8. customThe solvent was removed by evaporation in vacuum

Quellen und Nachweise

ORD-Eintrag
ord-ed1c017c29a641caa3214973ec92ce20
Quelldatensatz
uspto-grants-2007_01
Patentnummer
US07169810B2

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