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

HRID 468620Notes

Reaction equation

HRID 468620 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 methanesulfinate (103 g, 937 mmol) was combined with ethyl 2-chloropropionate (109 g, 892 mmol) in ethanol (350 mL) in a 500 mL one neck round bottom flask. The reaction was heated to 77° C. for 20 h, and then allowed to cool to room temperature. The solids were removed by filtration through celite, and the filter pad was washed with ethanol. 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, 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. customThe solids 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

Sources & evidence

ORD record
ord-1641bd842ab34a8480bf5f1831817473
Source dataset
uspto-grants-2014_01
Patent number
US08624034B2

Reaction notes

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