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

Temperature

77 °C

Sodium methyl sulfinate (103 g, 937 mmol) was combined with the ethyl 2-chloropropionate (109 g, 892 mmol) in EtOH (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 EtOH. 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 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).

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

ORD record

ord-1e724d66c7cf410d80aabe6e9113d4da

Source dataset

uspto-grants-2014_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08809333B2