Acetic Acid → 2-Methylsulphonyl-4-phenylbutyric acid ethyl ester

HRID 478036

Reaktionsgleichung

Reaktionsgleichung von HRID 478036
[CH2:1]([O:3][C:4](=[O:10])[CH2:5][S:6]([CH3:9])(=[O:8])=[O:7])[CH3:2].[OH-].[Na+].[C:13]1([CH2:19][CH2:20]Br)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(O)(=O)C>CN(C=O)C>[CH2:1]([O:3][C:4](=[O:10])[CH:5]([S:6]([CH3:9])(=[O:8])=[O:7])[CH2:20][CH2:19][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[CH3:2]

Komponenten

6

Edukt 4

HCID 176Acetic AcidHCID 7666Phenethyl bromideHCID 14798Sodium HydroxideHCID 78201Ethyl methanesulfonylacetate

Produkt 1

HCID 540490452-Methylsulphonyl-4-phenylbutyric acid ethyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel2×

Versuchsvorschrift

6.648 g of methylsulphonyl-acetic acid ethyl ester are added dropwise at -30°, within 30 minutes, to 1.745 g of sodium hydroxide dispersion (55% in oil) in 40 ml of DMF. The solution is subsequently stirred for 15 minutes, then heated and, within 150 minutes, under reflux, 7.4 g of 2-phenylethyl bromide in 10 ml of DMF are added dropwise thereto. The reaction mixture is then stirred for 20 minutes, acidified with 12 ml of glacial acetic acid and concentrated by evaporation. The residue is taken up in ethyl acetate, washed with water, dried over magnesium sulphate, concentrated by evaporation and purified by flash chromatography on 700 g of silica gel 60 (eluant D). 1H-NMR (DMSO-d6): 1.35 ppm (t, 3H), 2.6-2.9 (m, 2H); 3.75 (dxd, 1H); 4.25 (q, 2H)

Aufarbeitung

  1. temperatureheated and, within 150 minutes
  2. temperatureunder reflux
  3. stirringThe reaction mixture is then stirred for 20 minutes
  4. concentrationconcentrated by evaporation
  5. washwashed with water
  6. dry with materialdried over magnesium sulphate
  7. concentrationconcentrated by evaporation
  8. custompurified by flash chromatography on 700 g of silica gel 60 (eluant D)

Quellen und Nachweise

ORD-Eintrag
ord-d0930861d2ba43478dd4e4cb4a4fb6e7
Quelldatensatz
uspto-grants-1989_12
Patentnummer
US04889869

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