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

HRID 533497Notes

Reaction equation

HRID 533497 reaction equation
[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]

Participants

4

Reactant 2

HCID 10807Ethyl 2-chloropropionateHCID 2733271Sodium methanesulfinate

Product 1

HCID 10511577Ethyl 2-(methylsulfonyl)propanoateYield 73%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
77 °C

Procedure

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. 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, 3H) 1.67 (d, J=7.47 Hz, 3H) 3.05 (s, 3H) 3.83-3.92 (m, 1H) 4.18-4.37 (m, 2H).

Workup

  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
  5. customsolids were removed by filtration
  6. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-192d3482cb364884a4a52ca70f27df84
Source dataset
uspto-grants-2014_10
Patent number
US08853258B2

Reaction notes

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