Ethyl 2-chloropropionate → Ethyl 2-(methylsulfonyl)propanoate

HRID 84212

Reaktionsgleichung

Reaktionsgleichung von HRID 84212
[CH3:1][S:2]([O-:4])=[O:3].[Na+].Cl[CH:7]([CH3:13])[C:8]([O:10][CH2:11][CH3:12])=[O:9]>C(O)C>[CH3:1][S:2]([CH:7]([CH3:13])[C:8]([O:10][CH2:11][CH3:12])=[O:9])(=[O:4])=[O:3]

Komponenten

4

Edukt 2

HCID 10807Ethyl 2-chloropropionateHCID 2733271Sodium methanesulfinate

Produkt 1

HCID 10511577Ethyl 2-(methylsulfonyl)propanoateAusbeute 73 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
77 °C

Versuchsvorschrift

Sodium methyl sulfinate (103 g, 937 mmol) was combined with the ethyl 2-chloropropionate (109 g, 892 mmol) in ethanol (350 mL) in a 500 mL one neck round bottom flask. The reaction was warmed to 77° C. for 20 hours, and then allowed to cool to room temperature. Solids were removed by filtration through celite, and the filter pad was washed with ethanol and the combined filtrates were concentrated in vacuo. The crude product was suspended in diethyl ether (250 mL), and solids were removed by filtration. The filtrate was concentrated in vacuo to afford the title compound as a pale yellow oil (51 g, 73%). 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 1.32 (t, J=7.05 Hz, 3 H) 1.67 (d, J=7.47 Hz, 3 H) 3.05 (s, 3 H) 3.83-3.92 (m, 1 H) 4.18-4.37 (m, 2 H).

Aufarbeitung

  1. temperatureto cool to room temperature
  2. customSolids were removed by filtration through celite
  3. washthe filter pad was washed with ethanol
  4. concentrationthe combined filtrates were concentrated in vacuo
  5. customsolids were removed by filtration
  6. concentrationThe filtrate was concentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-8c63b41e16fa43a59d6d875d8a89b957
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08846933B2

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